Research Article Synthesis of Novel Symmetrical and ...carbonyl)benzoic acid b withdiethylamine a by...
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Research Article Synthesis of Novel Symmetrical and Unsymmetrical o-Phthalic Acid Diamides Padam Praveen Kumar, Yervala Dathu Reddy, Chittireddy Venkata Ramana Reddy, Bhoomireddy Rama Devi, and Pramod Kumar Dubey Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Kukatpally, Hyderabad, Andhra Pradesh 500085, India Correspondence should be addressed to Padam Praveen Kumar; [email protected] Received 23 January 2014; Revised 26 March 2014; Accepted 27 March 2014; Published 5 May 2014 Academic Editor: Joseph E. Saavedra Copyright © 2014 Padam Praveen Kumar et al. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Phthalic anhydride was treated with secondary amines in acetic acid yielding 2-(diethyl (or) 4-alkylpiperazine or morpholine-1- carbonyl) benzoic acids. e latter were reacted, again, with secondary amines and arylamines by using the coupling reagent HATU and Et 3 N as a base in DMF giving the novel symmetrical o-phthalic acid diamides [o-R 1 R 1 NCOC 6 H 4 CONR 1 R 1 ], unsymmetrical o- phthalic acid diamides [o-R 1 R 1 NCOC 6 H 4 CONR 1 R 2 ], and primary amidic-secondary amidic containing unsymmetrical o-phthalic acid diamides [o-R 1 R 1 NCOC 6 H 4 CONHAr], respectively. 1. Introduction Phthalic anhydride is used in the manufacture of dialkylph- thalates [1, 2] which find application as plasticisers for polymers like polyvinyl chloride (PVC) and polyvinylacetate (PVA). It is used in the manufacture of phenolphthalein indicator [3, 4], anthraquinone [5] (a versatile, raw materials in the dye industry [6]), and metal phthalocyanines [7]. Phthalocyanine compounds are used in a variety of appli- cations [7] in addition to their use as pigments, in paints [8] and in many types of dyestuffs [7]. Phthalic anhydride derivatives have been widely reported to possess beneficial pharmaceutical effects, like analgesic [9], anti-inflammatory [10] and antiviral effects [11]. Dunlap and Cummer reported [12] the preparation of symmetrical o-phthalic acid diamides [o- ArNHCOC 6 H 4 CONHAr] by the reaction of phthaloyl dichloride with two moles of aniline in ether at RT. Dann et al. reported [13] the preparation of symmetrical o-phthalic acid diamides by the reaction of phthaloyl dichloride with two moles of aniline in the presence of sodium fluoride in benzene under reflux for 1h. de Toranzo and Brieux reported [14] the synthesis of unsymmetrical diamides [ArNHCOC 6 H 4 CONHAr 1 ] by the reaction of phthalphenylisoimide with anilines in ether at RT. Reynolds reported [15] that unsymmetrical diamides [ArNHCOC 6 H 4 CONHAr 1 ] can be made by the reaction of N-arylphthalamic acid with the sodium salt of o- or p-methylaniline in an atmosphere of nitrogen for 1 h at 75 ∘ C. However, these methods suffer from drawbacks such as long reaction times, excess use of organic solvents, harsh refluxing conditions, and preparation of difficult starting materials from phthalic anhydride by the reaction with primary amines in the presence of trifluoroacetic anhydride. Keeping these facts in mind, we wish to report our results on reactions of phthalic anhydride with primary and secondary amines using HATU as a coupling reagent. Probably, this appears to be the first ever case of facile preparation of symmetrical and unsymmetrical o-phthalic acid diamides. e use of HATU as a coupling agent has been reported in the literature for reactions such as amide bond formation in solid phase synthesis [16–18] and peptides synthesis [19]. However, its use in the preparation of diamides from phthalic anhydride with amines has probably not been reported so far. Hindawi Publishing Corporation Organic Chemistry International Volume 2014, Article ID 576715, 9 pages http://dx.doi.org/10.1155/2014/576715
Transcript of Research Article Synthesis of Novel Symmetrical and ...carbonyl)benzoic acid b withdiethylamine a by...
Research ArticleSynthesis of Novel Symmetrical and Unsymmetrical o-PhthalicAcid Diamides
Padam Praveen Kumar Yervala Dathu Reddy Chittireddy Venkata Ramana ReddyBhoomireddy Rama Devi and Pramod Kumar Dubey
Department of Chemistry Jawaharlal Nehru Technological University Hyderabad College of Engineering Kukatpally HyderabadAndhra Pradesh 500085 India
Correspondence should be addressed to Padam Praveen Kumar padampraveenkugmailcom
Received 23 January 2014 Revised 26 March 2014 Accepted 27 March 2014 Published 5 May 2014
Academic Editor Joseph E Saavedra
Copyright copy 2014 Padam Praveen Kumar et al This is an open access article distributed under the Creative Commons AttributionLicense which permits unrestricted use distribution and reproduction in any medium provided the original work is properlycited
Phthalic anhydride was treated with secondary amines in acetic acid yielding 2-(diethyl (or) 4-alkylpiperazine or morpholine-1-carbonyl) benzoic acidsThe latter were reacted again with secondary amines and arylamines by using the coupling reagent HATUand Et
3N as a base in DMF giving the novel symmetrical o-phthalic acid diamides [o-R1R1NCOC6H4CONR1R1] unsymmetrical o-
phthalic acid diamides [o-R1R1NCOC6H4CONR1R2] and primary amidic-secondary amidic containing unsymmetrical o-phthalicacid diamides [o-R1R1NCOC6H4CONHAr] respectively
1 Introduction
Phthalic anhydride is used in the manufacture of dialkylph-thalates [1 2] which find application as plasticisers forpolymers like polyvinyl chloride (PVC) and polyvinylacetate(PVA) It is used in the manufacture of phenolphthaleinindicator [3 4] anthraquinone [5] (a versatile raw materialsin the dye industry [6]) and metal phthalocyanines [7]Phthalocyanine compounds are used in a variety of appli-cations [7] in addition to their use as pigments in paints[8] and in many types of dyestuffs [7] Phthalic anhydridederivatives have been widely reported to possess beneficialpharmaceutical effects like analgesic [9] anti-inflammatory[10] and antiviral effects [11]
Dunlap and Cummer reported [12] the preparationof symmetrical o-phthalic acid diamides [o-ArNHCOC
6H4CONHAr] by the reaction of phthaloyl
dichloride with two moles of aniline in ether at RTDann et al reported [13] the preparation of symmetricalo-phthalic acid diamides by the reaction of phthaloyldichloride with two moles of aniline in the presence ofsodium fluoride in benzene under reflux for 1 h de Toranzo
and Brieux reported [14] the synthesis of unsymmetricaldiamides [ArNHCOC
6H4CONHAr1] by the reaction
of phthalphenylisoimide with anilines in ether at RTReynolds reported [15] that unsymmetrical diamides[ArNHCOC
6H4CONHAr1] can be made by the reaction
of N-arylphthalamic acid with the sodium salt of o- orp-methylaniline in an atmosphere of nitrogen for 1 h at 75∘CHowever these methods suffer from drawbacks such as longreaction times excess use of organic solvents harsh refluxingconditions and preparation of difficult starting materialsfromphthalic anhydride by the reactionwith primary aminesin the presence of trifluoroacetic anhydride Keeping thesefacts in mind we wish to report our results on reactionsof phthalic anhydride with primary and secondary aminesusing HATU as a coupling reagent Probably this appearsto be the first ever case of facile preparation of symmetricaland unsymmetrical o-phthalic acid diamides The use ofHATU as a coupling agent has been reported in the literaturefor reactions such as amide bond formation in solid phasesynthesis [16ndash18] and peptides synthesis [19] However itsuse in the preparation of diamides from phthalic anhydridewith amines has probably not been reported so far
Hindawi Publishing CorporationOrganic Chemistry InternationalVolume 2014 Article ID 576715 9 pageshttpdxdoiorg1011552014576715
2 Organic Chemistry International
Table 1 Effect of coupling reagent tertiary base and temperature on condensation of 3a with 2b in DMF yielding 5a
Entry Coupling reagent Tertiary base Temp∘C Timemin 5a ()1 HATU Et3N 0ndash5 40ndash45 802 HATU Et3N RT 40ndash45 783 HATU DBU 0ndash5 55ndash65 704 HATU DBU RT 50ndash55 705 HATU Et3N 50ndash60 35ndash40 736 DCC mdash 0ndash5 120ndash130 457 DCC mdash RT 100ndash110 488 DCCHOBt mdash 0ndash5 110ndash120 509 DCCHOBt mdash RT 100ndash110 5010 DCCHOBt mdash 50ndash60 55ndash60 7211 EDCsdotHClHOBt Et3N 0ndash5 80ndash85 7012 EDCsdotHClHOBt Et3N RT 70ndash80 7013 EDCsdotHClHOBt DBU 0ndash5 70ndash80 6014 EDCsdotHClHOBt DBU RT 70ndash75 6515 EDCsdotHClHOBt Et3N 50ndash60 65ndash70 7216 HBTU Et3N 0ndash5 70ndash75 7017 HBTU Et3N RT 65ndash70 7018 HBTU DBU 0ndash5 70ndash80 6519 HBTU DBU RT 65ndash75 6520 HBTU Et3N 50ndash60 50ndash55 7021 PTSA mdash 0ndash5 120ndash125 mdash22 PTSA mdash RT 120ndash125 mdash23 PPA mdash 100 60ndash65 40
Table 2 Characterization data reaction time and yields of 3andash3e obtained 1 and 2andash2e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 2a 3a 10ndash12 85 145ndash1482 2b 3b 12ndash15 85 gt2203 2c 3c 15ndash18 83 gt2204 2d 3d 15ndash18 80 gt2205 2e 3e 15ndash20 81 gt220= Refers to yields of crude products only
2 Results and Discussion
Phthalic anhydride 1 was treated with the secondary amines2andash2e in acetic acid at RT for 10ndash15min resulting in the for-mation of 2-(diethyl (or) 4-alkylpiperazine (or) morpholine-1-carbonyl)benzoic acid 3andash3e Reaction of 3awith the piper-azine 2b in the presence of o-(7-azabenzotriazol-1-yl)-1133-tetramethyluroniumhexafluorophosphate (HATU) and Et
3N
at 0ndash5∘C for 40ndash45min in DMF gave 5a Alternativelythis compound was prepared by treating 2-(piperazine-1-carbonyl)benzoic acid 3b withdiethylamine 2a by HATUand Et
3N at 0ndash5∘C for 40ndash45min in DMF to form NN-
diethyl-2-(piperazine-1-carbonyl)benzamide 5a This reac-tion was examined by carrying out the condensation of 2-(diethylcarbonyl)benzoic acid 3a (1mmol) with piperazine2b (1mmol) in the presence different coupling reagents(HATU EDCHClHOBt (1-hydroxybenzotriazole) DCC(NN1015840-dicyclohexylcarbodiimide) HBTU and PTSA (4-methylbenzenesulfonic acid)) and tertiary bases (Et
3N and
DBU (2 3 4 6 7 8 9 10-octahydropyrimido [1 2-a] azepine)at different temperatures in DMF as a solvent (Table 1) witha view to study the generalisation of condensation between3 and 2 However coupling of 3a with 2b in the presence ofHATU and Et
3N at 0ndash5∘C for 40ndash45min in DMF was found
to be the best method giving 5a in quality and yield (ge80)(Table 1 entry 1)
Using the above-stated optimised conditions 3andash3e werecondensed into 2andash2eusingHATUandEt
3Nat 0ndash5∘C for 40ndash
65min in DMF yielding 4andash4e and 5andash5j (Scheme 1) (Tables2 and 3) in excellent yieldThe structures of the products havebeen established on the basis of their spectral and analyticaldata (Please see experimental section)
Condensation of 3andash3e with arylamines 6andash6e inthe presence of HATU and Et
3N at 0ndash5∘C for 40ndash
55min in DMF gave primary amidic-secondary amidiccontaining unsymmetrical o-phthalic acid diamides [o-R1R1NCOC
6H4CONHAr] 7andash7y (Scheme 2) (Table 4)
Organic Chemistry International 3
O
O
O
O
O
OH
HN N
O
O
N
N
HN
O
O
N
N
HN
(1)
(2)
(3)
(4)
(5)
CH3COOHRT10ndash15min
HATUEt3NDMF40ndash65min
HATUEt3NDMF40ndash65min
(2)
(2)
Scheme 1 Synthetic routes to 4andash4e and 5andash5j
The structures of the products have been established onthe basis of their spectral and analytical data An alternateprotocol was attemptedto synthesize 7andash7y by treatment of1 with aniline 6a in acetic acid at 0ndash5∘C for 10ndash15min whichgave 2-(phenylcarbamoyl)benzoic acid 8a18 and subsequentreaction of 8awith diethylamine 2a in the presence of HATUand Et
3N at RT for 20ndash25min in DMF which resulted in the
formation of 2-phenylisoindoline-1 3-dione 9a18
3 Conclusion
In conclusion we have developed novel syntheses of sym-metrical 4andash4e and unsymmetrical 5andash5j and 7andash7y o-phthalic acid diamides This approach presents a simple anduseful synthetic process which requires a few minutes ofreaction time easily available starting materials and straightforward and easy workup procedure Probably this appearsto be the first ever case of facile preparation of symmetricaland unsymmetrical o-phthalic acid diamides The use ofHATU as a coupling agent has been reported in the liter-ature for reactions such as amide bond formation in solidphase synthesis and peptides synthesis However its use inthe preparation of diamides from phthalic anhydride withamines has probably not been reported so far The overallyields of these compounds are very good
4 Materials and Methods
Melting points are uncorrected and were determined in opencapillary tubes in sulphuric acid bath TLC was run on silicagel-G visualization was done using iodine or UV light andIR spectra were recorded using PerkinElmer 1000 instrumentin KBr pellets 1HNMR spectra were recorded in DMSO-d
6
using TMS as internal standard using 400MHz spectrometerMass spectra were recorded on Agilent-LCMS instrumentunder CI conditions and given by 119876 + 1 values only Starting1 2 and 6 were obtained from commercial sources and usedas such
41 Preparation of 3andash3e A mixture of 1a (10mM) 2andash2e (10Mm) and CH
3COOH (20mL) was stirred at RT for
10ndash20min A colourless solid separated out from reactionmixture which was filtered washed with hexane (10mL) anddried The crude product was recrystallized from suitablesolvent to obtain 3andash3e
42 Preparation of 4andash4e amp 5andash5j A mixture of 3andash3e(10mM) 2andash2e (10mM)HATU (10mM) Et
3N (10mM) and
DMF (15mL) was stirred at 0ndash5∘C for 40ndash65min Then ice-cold water (50mL) was added to the reaction mixture Theseparated solid was filtered washed with water (10mL) anddried The product was recrystallized from a suitable solventto obtain 4andash4e and 5andash5j
43 Preparation of 7andash7y A mixture of 3andash3e (10mM)6andash6e (10mM) HATU (10mM) Et
3N (10mM) and DMF
(15mL) was stirred at 0ndash5∘C for 40ndash55min Then ice-cold water (50mL) was added to the reaction mixture Theseparated solid was filtered washed with water (10mL) anddried The product was recrystallized from a suitable solventto obtain 7andash7y
5 Supporting Information
3a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 08 (t 3H ndashCH
3) 120575 12 (t 3H ndashCH
3) 120575 30 (q
2H ndashCH2) 120575 36 (q 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 1300
(s 1H ndashCOOH D2O exchangeable) 1012 (s 1H ndashNH D2Oexchangeable) 13C NMR (DMSO-d
6 400MHz) 123 414
1231 1285 1293 1295 1602 1655 Ms 119898119911 = 222 (M+ +1)
3b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1725 cmminus1 (sharp strong ndashCOndash ofacid group) 1670 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 22 (s 1H ndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
4H Ar-H) 1300 (s 1H ndashCOOH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 494 501 514 519 1241 1255
1273 1285 1612 1648 Ms119898119911 = 235 (M+ + 1)
4 Organic Chemistry International
O
N
O
O
O
O
N
(7)
(8)
(9)
NH-Ar
Ar
OH
(6)(6)
NH-Ar
HN(2)
HN HNC2H5
C2H5
N H CH3 O= HN HN N C2H5 HN N HN(2) (2)
(a) (b) (c) (d) (e)
(6) (a) (b) (c) (d) (e)
HN
Ar = ndashC6H5ndashC6H4ndashCH3(p)ndashC6H4ndashCH3(O)ndashC6H4ndashCl(p)ndashC6H4ndashBr(p)
O
NOH
(3)
+ Et3N
OminusEt3NH
O
O
OminusN
NO
NN
N N
N
O
O
O
O
N
N
NN N
N
NN N
NHO
minus
N
NO
ON
NON
NNN
O NN
minus
N
NN
N
O
O
O
HN H2N-Ar(2) (5)
NNNN
∙∙
∙∙
minusO
NNNN
minus
Ominus
O
N
O H
O
NN
O(4) and (5)
O
N
O
minusH+
O
NNH-Ar
(7) O
+
N +NH-Ar
Ominus
minusH+
N
O
O
O
OHN
(1)CH3COOHRT10ndash15min
(2)
O
O
OHN
(3)
H2N-Ar
HATUEt3NDMF40ndash55min
HATUEt3NDMF20ndash25min
H2N-Ar
CH3COOHRT10ndash15min
minus
Plausible mechanism for 4 5 and 7 from 3
Scheme 2 Synthetic routes to 7andash7y
3c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1730 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 12 (t 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 4H Ar-H) 132 (s 1H ndashCOOH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 494
501 509 519 522 1231 1245 1253 1275 1632 1648 Ms119898119911 = 263 (M+ + 1)
3d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOH groups put together) 1720 cmminus1 (sharp strong ndashCOndashof acid group) 1660 cmminus1 (sharp storng ndashCOndash of amide
Organic Chemistry International 5
Table 3 Characterization data reaction time and yields of 4andash4e and 5andash5j obtained from 3andash3e and 2andash2e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 2a 4a 40ndash45 85 gt2202 3b 2b 4b 40ndash45 85 gt2203 3c 2c 4c 50ndash55 80 gt2204 3d 2d 4d 50ndash55 80 gt2205 3e 2e 4e 40ndash45 80 gt2206 3a 2b 5a 40ndash45 85 gt2207 3a 2c 5b 50ndash55 81 110ndash1128 3a 2d 5c 50ndash55 84 115ndash1189 3a 2e 5d 50ndash55 85 80ndash8210 3b 2a 5a 40ndash45 83 gt22011 3b 2c 5e 50ndash55 84 gt22012 3b 2d 5f 50ndash55 85 gt22013 3b 2e 5g 60ndash65 85 85ndash8714 3c 2a 5b 60ndash65 81 110ndash11215 3c 2b 5e 50ndash55 83 gt22016 3c 2d 5h 50ndash55 85 gt22017 3c 2e 5i 50ndash55 85 90ndash9218 3d 2a 5c 60ndash65 80 115ndash11819 3d 2b 5f 50ndash55 80 gt22020 3d 2c 5h 40ndash45 85 gt22021 3d 2e 5j 40ndash45 83 gt22022 3e 2a 5d 40ndash45 80 80ndash8223 3e 2b 5g 50ndash55 84 85ndash8724 3e 2c 5i 50ndash55 84 90ndash9225 3e 2d 5j 40ndash45 83 gt220= Refers to yields of crude products only
group) 1H-NMR 120575 16 (t 3H ndashCH3) 120575 30 (t 2H ndashCH
2) 120575
32 (t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 4H Ar-H) 131 (s 1H ndashCOOH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 394 551 559 559 552
1261 1275 1283 1295 1602 1658 Ms119898119911 = 249 (M+ + 1)3e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH and
ndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t
2H ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 131
(s 1H ndashCOOH D2O exchangeable) 13C NMR (DMSO-d6
400MHz) 502 506 719 722 1251 1255 1263 1275 16221648 Ms119898119911 = 236 (M+ + 1)
4a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 6HndashCH3 ndashCH
3) 120575 14 (t 6H ndashCH
3 ndashCH
3) 120575 28 (q 4H ndashCH
2
ndashCH2) 120575 32 (q 4H ndashCH
2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13C
NMR (DMSO-d6 400MHz) 129 141 316 367 391 435
1253 1265 1271 1293 1636 1696 Ms119898119911 = 277 (M+ + 1)4b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1685 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22
(s 2H ndashNH ndashNH) 120575 30 (t 8H Four ndashCH2groups) 120575 34
(t 8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 474 486 497 509 515 524 1253
1255 1271 1286 1643 1676 Ms119898119911 = 303 (M+ + 1)4c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1660 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 13 (t 6HndashCH3 ndashCH
3) 120575 28 (q 4H ndashCH
2 ndashCH
2) 120575 32 (t 8H Four
ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80 (m
4H Ar-H) 13C NMR (DMSO-d6 400MHz) 123 161 464
476 487 491 505 514 1233 1245 1281 1289 1646 1686Ms119898119911 = 359 (M+ + 1)
4d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 8H Four ndashCH
2groups) 120575 32 (t
8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 323 334 484 489 497 505 524
553 1253 1256 1283 1299 1652 1693 Ms 119898119911 = 331(M+ + 1)
4e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t 8H
6 Organic Chemistry International
Table 4 Characterization data reaction time and yield of 7andash7y obtained from 3andash3e and 6andash6e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 6a 7a 40ndash45 85 115ndash1182 3b 6a 7b 50ndash55 82 120ndash1233 3c 6a 7c 40ndash45 84 123ndash1254 3d 6a 7d 50ndash55 85 gt2205 3e 6a 7e 50ndash55 80 126ndash1286 3a 6b 7f 40ndash45 83 128ndash1307 3b 6b 7g 40ndash45 82 138ndash1408 3c 6b 7h 50ndash55 82 120ndash1239 3d 6b 7i 50ndash55 85 gt22010 3e 6b 7j 40ndash45 80 122ndash12411 3a 6c 7k 50ndash55 82 120ndash12412 3b 6c 7l 40ndash45 85 130ndash13213 3c 6c 7m 50ndash55 85 170ndash17414 3d 6c 7n 50ndash55 80 gt22015 3e 6c 7o 40ndash45 80 140ndash14316 3a 6d 7p 40ndash45 80 125ndash12817 3b 6d 7q 50ndash55 82 135ndash13718 3c 6d 7r 50ndash55 82 180ndash18319 3d 6d 7s 40ndash45 80 gt22020 3e 6d 7t 40ndash45 85 142ndash14521 3a 6e 7u 40ndash45 84 128ndash13022 3b 6e 7v 40ndash45 85 133ndash13523 3c 6e 7w 50ndash55 80 190ndash19224 3d 6e 7x 50ndash55 82 gt22025 3e 6e 7y 40ndash45 84 145ndash148= Refers to yields of crude products only
Four ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80
(m 4H Ar-H) 13C NMR (DMSO-d6 400MHz) 493 499
507 528 559 568 1254 1263 1274 1289 1642 1673 Ms119898119911 = 305 (M+ + 1)
5a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1660 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 22 (s 1H ndashNH) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 129 317 435 446 511 525 1231 1243 1283
1296 1617 1655 Ms119898119911 = 290 (M+ + 1)5b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 14 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2)
120575 30 (t 4H ndashCH2 ndashCH
2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34
(q 2H ndashCH2) 120575 36 (q 2H ndashCH
2 ndashCH
2) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 129 136 315 445
456 486 541 555 1236 1253 1283 1296 1627 1654 Ms119898119911 = 318 (M+ + 1)
5c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 18 (t 3H ndashCH
3) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 139 327 415 446 455 531 545 1223 1253
1292 1299 1647 1664 Ms119898119911 = 304 (M+ + 1)5d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 4H ndashCH
2 ndashCH
2) 120575 32 (t 4H ndash
CH2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q 2H ndashCH
2 ndashCH
2)
70ndash80 (m 4H Ar-H) 13CNMR (DMSO-d6 400MHz) 132
334 443 452 501 524 1242 1235 1254 1257 1603 1656Ms119898119911 = 291 (M+ + 1)
5e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 22 (q 2H ndashCH
2) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 124 294 302 317 334 343 425
436 502 512 1241 1252 1273 1293 1603 1642Ms119898119911 =331 (M+ + 1)
5f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1
Organic Chemistry International 7
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 284 314 325 333 354 414 424 514 5231252 1261 1283 1292 1616 1651 Ms119898119911 = 317 (M+ + 1)
5g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 28ndash36 (t 16H eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 301 313 335 342
426 438 501 514 1232 1251 1282 1293 1603 1653 Ms119898119911 = 304 (M+ + 1)
5h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 18 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 132 286 295 322 337 345 354
435 445 535 546 1255 1264 1269 1295 1613 1659 Ms119898119911 = 345 (M+ + 1)
5i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 132 294 312 322 332 345 427 448 509 5191243 1259 1278 1290 1607 1689 Ms119898119911 = 332 (M+ + 1)
5j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 28ndash36 (t 16H Eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H)13CNMR (DMSO-d6 400MHz) 284 332 347 354
393 445 476 532 552 1271 1282 1293 1299 1633 1694Ms119898119911 = 318 (M+ + 1)
7a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t6H ndashCH
3 ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34 (q 2H ndashCH
2)
70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 122 134 379 425 1234
1262 1278 1281 1285 1303 1341 1374 1391 1658 1692Ms119898119911 = 297 (M+ + 1)
7b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H
ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 104 (s 1H
ndashNH D2O exchangeable)13C NMR (DMSO-d6 400MHz)
493 503 515 513 1243 1245 1255 1264 1273 1285 12951299 1315 1632 1645 Ms119898119911 = 310 (M+ + 1)
7c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 26 (q 2H ndashCH
2) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 126 445 473 485 505 513 1203
1227 1254 1263 1277 1283 1292 1309 1314 1606 1649Ms119898119911 = 338 (M+ + 1)
7d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
345 464 472 486 502 1212 1234 1239 1246 1256 12631282 1319 1324 1642 1692 Ms119898119911 = 324 (M+ + 1)
7e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1660 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 8H Ar-H) 1300 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 503 513
715 723 1203 1212 1242 1256 1281 1289 1291 12991314 1651 1663 Ms119898119911 = 311 (M+ + 1)
7f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1644 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 126
138 194 399 436 1236 1246 1252 1266 1276 1298 13121335 1365 1667 1683 Ms119898119911 = 311 (M+ + 1)
7g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 205 445 493 505 515 1202 1224
1234 1245 1253 1266 1285 1301 1335 1637 1666 Ms119898119911 = 324 (M+ + 1)
7h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 122 193
442 476 483 512 522 1193 1213 1242 1249 1262 12711304 1313 1323 1611 1651 Ms119898119911 = 352 (M+ + 1)
7i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 184 354 454 463 473 513 1201
1222 1226 1245 1247 1274 1286 1310 1328 1646 1699Ms119898119911 = 338 (M+ + 1)
7j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
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Organic Chemistry International
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2 Organic Chemistry International
Table 1 Effect of coupling reagent tertiary base and temperature on condensation of 3a with 2b in DMF yielding 5a
Entry Coupling reagent Tertiary base Temp∘C Timemin 5a ()1 HATU Et3N 0ndash5 40ndash45 802 HATU Et3N RT 40ndash45 783 HATU DBU 0ndash5 55ndash65 704 HATU DBU RT 50ndash55 705 HATU Et3N 50ndash60 35ndash40 736 DCC mdash 0ndash5 120ndash130 457 DCC mdash RT 100ndash110 488 DCCHOBt mdash 0ndash5 110ndash120 509 DCCHOBt mdash RT 100ndash110 5010 DCCHOBt mdash 50ndash60 55ndash60 7211 EDCsdotHClHOBt Et3N 0ndash5 80ndash85 7012 EDCsdotHClHOBt Et3N RT 70ndash80 7013 EDCsdotHClHOBt DBU 0ndash5 70ndash80 6014 EDCsdotHClHOBt DBU RT 70ndash75 6515 EDCsdotHClHOBt Et3N 50ndash60 65ndash70 7216 HBTU Et3N 0ndash5 70ndash75 7017 HBTU Et3N RT 65ndash70 7018 HBTU DBU 0ndash5 70ndash80 6519 HBTU DBU RT 65ndash75 6520 HBTU Et3N 50ndash60 50ndash55 7021 PTSA mdash 0ndash5 120ndash125 mdash22 PTSA mdash RT 120ndash125 mdash23 PPA mdash 100 60ndash65 40
Table 2 Characterization data reaction time and yields of 3andash3e obtained 1 and 2andash2e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 2a 3a 10ndash12 85 145ndash1482 2b 3b 12ndash15 85 gt2203 2c 3c 15ndash18 83 gt2204 2d 3d 15ndash18 80 gt2205 2e 3e 15ndash20 81 gt220= Refers to yields of crude products only
2 Results and Discussion
Phthalic anhydride 1 was treated with the secondary amines2andash2e in acetic acid at RT for 10ndash15min resulting in the for-mation of 2-(diethyl (or) 4-alkylpiperazine (or) morpholine-1-carbonyl)benzoic acid 3andash3e Reaction of 3awith the piper-azine 2b in the presence of o-(7-azabenzotriazol-1-yl)-1133-tetramethyluroniumhexafluorophosphate (HATU) and Et
3N
at 0ndash5∘C for 40ndash45min in DMF gave 5a Alternativelythis compound was prepared by treating 2-(piperazine-1-carbonyl)benzoic acid 3b withdiethylamine 2a by HATUand Et
3N at 0ndash5∘C for 40ndash45min in DMF to form NN-
diethyl-2-(piperazine-1-carbonyl)benzamide 5a This reac-tion was examined by carrying out the condensation of 2-(diethylcarbonyl)benzoic acid 3a (1mmol) with piperazine2b (1mmol) in the presence different coupling reagents(HATU EDCHClHOBt (1-hydroxybenzotriazole) DCC(NN1015840-dicyclohexylcarbodiimide) HBTU and PTSA (4-methylbenzenesulfonic acid)) and tertiary bases (Et
3N and
DBU (2 3 4 6 7 8 9 10-octahydropyrimido [1 2-a] azepine)at different temperatures in DMF as a solvent (Table 1) witha view to study the generalisation of condensation between3 and 2 However coupling of 3a with 2b in the presence ofHATU and Et
3N at 0ndash5∘C for 40ndash45min in DMF was found
to be the best method giving 5a in quality and yield (ge80)(Table 1 entry 1)
Using the above-stated optimised conditions 3andash3e werecondensed into 2andash2eusingHATUandEt
3Nat 0ndash5∘C for 40ndash
65min in DMF yielding 4andash4e and 5andash5j (Scheme 1) (Tables2 and 3) in excellent yieldThe structures of the products havebeen established on the basis of their spectral and analyticaldata (Please see experimental section)
Condensation of 3andash3e with arylamines 6andash6e inthe presence of HATU and Et
3N at 0ndash5∘C for 40ndash
55min in DMF gave primary amidic-secondary amidiccontaining unsymmetrical o-phthalic acid diamides [o-R1R1NCOC
6H4CONHAr] 7andash7y (Scheme 2) (Table 4)
Organic Chemistry International 3
O
O
O
O
O
OH
HN N
O
O
N
N
HN
O
O
N
N
HN
(1)
(2)
(3)
(4)
(5)
CH3COOHRT10ndash15min
HATUEt3NDMF40ndash65min
HATUEt3NDMF40ndash65min
(2)
(2)
Scheme 1 Synthetic routes to 4andash4e and 5andash5j
The structures of the products have been established onthe basis of their spectral and analytical data An alternateprotocol was attemptedto synthesize 7andash7y by treatment of1 with aniline 6a in acetic acid at 0ndash5∘C for 10ndash15min whichgave 2-(phenylcarbamoyl)benzoic acid 8a18 and subsequentreaction of 8awith diethylamine 2a in the presence of HATUand Et
3N at RT for 20ndash25min in DMF which resulted in the
formation of 2-phenylisoindoline-1 3-dione 9a18
3 Conclusion
In conclusion we have developed novel syntheses of sym-metrical 4andash4e and unsymmetrical 5andash5j and 7andash7y o-phthalic acid diamides This approach presents a simple anduseful synthetic process which requires a few minutes ofreaction time easily available starting materials and straightforward and easy workup procedure Probably this appearsto be the first ever case of facile preparation of symmetricaland unsymmetrical o-phthalic acid diamides The use ofHATU as a coupling agent has been reported in the liter-ature for reactions such as amide bond formation in solidphase synthesis and peptides synthesis However its use inthe preparation of diamides from phthalic anhydride withamines has probably not been reported so far The overallyields of these compounds are very good
4 Materials and Methods
Melting points are uncorrected and were determined in opencapillary tubes in sulphuric acid bath TLC was run on silicagel-G visualization was done using iodine or UV light andIR spectra were recorded using PerkinElmer 1000 instrumentin KBr pellets 1HNMR spectra were recorded in DMSO-d
6
using TMS as internal standard using 400MHz spectrometerMass spectra were recorded on Agilent-LCMS instrumentunder CI conditions and given by 119876 + 1 values only Starting1 2 and 6 were obtained from commercial sources and usedas such
41 Preparation of 3andash3e A mixture of 1a (10mM) 2andash2e (10Mm) and CH
3COOH (20mL) was stirred at RT for
10ndash20min A colourless solid separated out from reactionmixture which was filtered washed with hexane (10mL) anddried The crude product was recrystallized from suitablesolvent to obtain 3andash3e
42 Preparation of 4andash4e amp 5andash5j A mixture of 3andash3e(10mM) 2andash2e (10mM)HATU (10mM) Et
3N (10mM) and
DMF (15mL) was stirred at 0ndash5∘C for 40ndash65min Then ice-cold water (50mL) was added to the reaction mixture Theseparated solid was filtered washed with water (10mL) anddried The product was recrystallized from a suitable solventto obtain 4andash4e and 5andash5j
43 Preparation of 7andash7y A mixture of 3andash3e (10mM)6andash6e (10mM) HATU (10mM) Et
3N (10mM) and DMF
(15mL) was stirred at 0ndash5∘C for 40ndash55min Then ice-cold water (50mL) was added to the reaction mixture Theseparated solid was filtered washed with water (10mL) anddried The product was recrystallized from a suitable solventto obtain 7andash7y
5 Supporting Information
3a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 08 (t 3H ndashCH
3) 120575 12 (t 3H ndashCH
3) 120575 30 (q
2H ndashCH2) 120575 36 (q 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 1300
(s 1H ndashCOOH D2O exchangeable) 1012 (s 1H ndashNH D2Oexchangeable) 13C NMR (DMSO-d
6 400MHz) 123 414
1231 1285 1293 1295 1602 1655 Ms 119898119911 = 222 (M+ +1)
3b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1725 cmminus1 (sharp strong ndashCOndash ofacid group) 1670 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 22 (s 1H ndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
4H Ar-H) 1300 (s 1H ndashCOOH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 494 501 514 519 1241 1255
1273 1285 1612 1648 Ms119898119911 = 235 (M+ + 1)
4 Organic Chemistry International
O
N
O
O
O
O
N
(7)
(8)
(9)
NH-Ar
Ar
OH
(6)(6)
NH-Ar
HN(2)
HN HNC2H5
C2H5
N H CH3 O= HN HN N C2H5 HN N HN(2) (2)
(a) (b) (c) (d) (e)
(6) (a) (b) (c) (d) (e)
HN
Ar = ndashC6H5ndashC6H4ndashCH3(p)ndashC6H4ndashCH3(O)ndashC6H4ndashCl(p)ndashC6H4ndashBr(p)
O
NOH
(3)
+ Et3N
OminusEt3NH
O
O
OminusN
NO
NN
N N
N
O
O
O
O
N
N
NN N
N
NN N
NHO
minus
N
NO
ON
NON
NNN
O NN
minus
N
NN
N
O
O
O
HN H2N-Ar(2) (5)
NNNN
∙∙
∙∙
minusO
NNNN
minus
Ominus
O
N
O H
O
NN
O(4) and (5)
O
N
O
minusH+
O
NNH-Ar
(7) O
+
N +NH-Ar
Ominus
minusH+
N
O
O
O
OHN
(1)CH3COOHRT10ndash15min
(2)
O
O
OHN
(3)
H2N-Ar
HATUEt3NDMF40ndash55min
HATUEt3NDMF20ndash25min
H2N-Ar
CH3COOHRT10ndash15min
minus
Plausible mechanism for 4 5 and 7 from 3
Scheme 2 Synthetic routes to 7andash7y
3c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1730 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 12 (t 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 4H Ar-H) 132 (s 1H ndashCOOH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 494
501 509 519 522 1231 1245 1253 1275 1632 1648 Ms119898119911 = 263 (M+ + 1)
3d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOH groups put together) 1720 cmminus1 (sharp strong ndashCOndashof acid group) 1660 cmminus1 (sharp storng ndashCOndash of amide
Organic Chemistry International 5
Table 3 Characterization data reaction time and yields of 4andash4e and 5andash5j obtained from 3andash3e and 2andash2e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 2a 4a 40ndash45 85 gt2202 3b 2b 4b 40ndash45 85 gt2203 3c 2c 4c 50ndash55 80 gt2204 3d 2d 4d 50ndash55 80 gt2205 3e 2e 4e 40ndash45 80 gt2206 3a 2b 5a 40ndash45 85 gt2207 3a 2c 5b 50ndash55 81 110ndash1128 3a 2d 5c 50ndash55 84 115ndash1189 3a 2e 5d 50ndash55 85 80ndash8210 3b 2a 5a 40ndash45 83 gt22011 3b 2c 5e 50ndash55 84 gt22012 3b 2d 5f 50ndash55 85 gt22013 3b 2e 5g 60ndash65 85 85ndash8714 3c 2a 5b 60ndash65 81 110ndash11215 3c 2b 5e 50ndash55 83 gt22016 3c 2d 5h 50ndash55 85 gt22017 3c 2e 5i 50ndash55 85 90ndash9218 3d 2a 5c 60ndash65 80 115ndash11819 3d 2b 5f 50ndash55 80 gt22020 3d 2c 5h 40ndash45 85 gt22021 3d 2e 5j 40ndash45 83 gt22022 3e 2a 5d 40ndash45 80 80ndash8223 3e 2b 5g 50ndash55 84 85ndash8724 3e 2c 5i 50ndash55 84 90ndash9225 3e 2d 5j 40ndash45 83 gt220= Refers to yields of crude products only
group) 1H-NMR 120575 16 (t 3H ndashCH3) 120575 30 (t 2H ndashCH
2) 120575
32 (t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 4H Ar-H) 131 (s 1H ndashCOOH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 394 551 559 559 552
1261 1275 1283 1295 1602 1658 Ms119898119911 = 249 (M+ + 1)3e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH and
ndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t
2H ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 131
(s 1H ndashCOOH D2O exchangeable) 13C NMR (DMSO-d6
400MHz) 502 506 719 722 1251 1255 1263 1275 16221648 Ms119898119911 = 236 (M+ + 1)
4a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 6HndashCH3 ndashCH
3) 120575 14 (t 6H ndashCH
3 ndashCH
3) 120575 28 (q 4H ndashCH
2
ndashCH2) 120575 32 (q 4H ndashCH
2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13C
NMR (DMSO-d6 400MHz) 129 141 316 367 391 435
1253 1265 1271 1293 1636 1696 Ms119898119911 = 277 (M+ + 1)4b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1685 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22
(s 2H ndashNH ndashNH) 120575 30 (t 8H Four ndashCH2groups) 120575 34
(t 8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 474 486 497 509 515 524 1253
1255 1271 1286 1643 1676 Ms119898119911 = 303 (M+ + 1)4c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1660 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 13 (t 6HndashCH3 ndashCH
3) 120575 28 (q 4H ndashCH
2 ndashCH
2) 120575 32 (t 8H Four
ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80 (m
4H Ar-H) 13C NMR (DMSO-d6 400MHz) 123 161 464
476 487 491 505 514 1233 1245 1281 1289 1646 1686Ms119898119911 = 359 (M+ + 1)
4d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 8H Four ndashCH
2groups) 120575 32 (t
8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 323 334 484 489 497 505 524
553 1253 1256 1283 1299 1652 1693 Ms 119898119911 = 331(M+ + 1)
4e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t 8H
6 Organic Chemistry International
Table 4 Characterization data reaction time and yield of 7andash7y obtained from 3andash3e and 6andash6e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 6a 7a 40ndash45 85 115ndash1182 3b 6a 7b 50ndash55 82 120ndash1233 3c 6a 7c 40ndash45 84 123ndash1254 3d 6a 7d 50ndash55 85 gt2205 3e 6a 7e 50ndash55 80 126ndash1286 3a 6b 7f 40ndash45 83 128ndash1307 3b 6b 7g 40ndash45 82 138ndash1408 3c 6b 7h 50ndash55 82 120ndash1239 3d 6b 7i 50ndash55 85 gt22010 3e 6b 7j 40ndash45 80 122ndash12411 3a 6c 7k 50ndash55 82 120ndash12412 3b 6c 7l 40ndash45 85 130ndash13213 3c 6c 7m 50ndash55 85 170ndash17414 3d 6c 7n 50ndash55 80 gt22015 3e 6c 7o 40ndash45 80 140ndash14316 3a 6d 7p 40ndash45 80 125ndash12817 3b 6d 7q 50ndash55 82 135ndash13718 3c 6d 7r 50ndash55 82 180ndash18319 3d 6d 7s 40ndash45 80 gt22020 3e 6d 7t 40ndash45 85 142ndash14521 3a 6e 7u 40ndash45 84 128ndash13022 3b 6e 7v 40ndash45 85 133ndash13523 3c 6e 7w 50ndash55 80 190ndash19224 3d 6e 7x 50ndash55 82 gt22025 3e 6e 7y 40ndash45 84 145ndash148= Refers to yields of crude products only
Four ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80
(m 4H Ar-H) 13C NMR (DMSO-d6 400MHz) 493 499
507 528 559 568 1254 1263 1274 1289 1642 1673 Ms119898119911 = 305 (M+ + 1)
5a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1660 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 22 (s 1H ndashNH) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 129 317 435 446 511 525 1231 1243 1283
1296 1617 1655 Ms119898119911 = 290 (M+ + 1)5b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 14 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2)
120575 30 (t 4H ndashCH2 ndashCH
2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34
(q 2H ndashCH2) 120575 36 (q 2H ndashCH
2 ndashCH
2) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 129 136 315 445
456 486 541 555 1236 1253 1283 1296 1627 1654 Ms119898119911 = 318 (M+ + 1)
5c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 18 (t 3H ndashCH
3) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 139 327 415 446 455 531 545 1223 1253
1292 1299 1647 1664 Ms119898119911 = 304 (M+ + 1)5d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 4H ndashCH
2 ndashCH
2) 120575 32 (t 4H ndash
CH2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q 2H ndashCH
2 ndashCH
2)
70ndash80 (m 4H Ar-H) 13CNMR (DMSO-d6 400MHz) 132
334 443 452 501 524 1242 1235 1254 1257 1603 1656Ms119898119911 = 291 (M+ + 1)
5e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 22 (q 2H ndashCH
2) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 124 294 302 317 334 343 425
436 502 512 1241 1252 1273 1293 1603 1642Ms119898119911 =331 (M+ + 1)
5f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1
Organic Chemistry International 7
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 284 314 325 333 354 414 424 514 5231252 1261 1283 1292 1616 1651 Ms119898119911 = 317 (M+ + 1)
5g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 28ndash36 (t 16H eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 301 313 335 342
426 438 501 514 1232 1251 1282 1293 1603 1653 Ms119898119911 = 304 (M+ + 1)
5h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 18 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 132 286 295 322 337 345 354
435 445 535 546 1255 1264 1269 1295 1613 1659 Ms119898119911 = 345 (M+ + 1)
5i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 132 294 312 322 332 345 427 448 509 5191243 1259 1278 1290 1607 1689 Ms119898119911 = 332 (M+ + 1)
5j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 28ndash36 (t 16H Eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H)13CNMR (DMSO-d6 400MHz) 284 332 347 354
393 445 476 532 552 1271 1282 1293 1299 1633 1694Ms119898119911 = 318 (M+ + 1)
7a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t6H ndashCH
3 ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34 (q 2H ndashCH
2)
70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 122 134 379 425 1234
1262 1278 1281 1285 1303 1341 1374 1391 1658 1692Ms119898119911 = 297 (M+ + 1)
7b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H
ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 104 (s 1H
ndashNH D2O exchangeable)13C NMR (DMSO-d6 400MHz)
493 503 515 513 1243 1245 1255 1264 1273 1285 12951299 1315 1632 1645 Ms119898119911 = 310 (M+ + 1)
7c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 26 (q 2H ndashCH
2) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 126 445 473 485 505 513 1203
1227 1254 1263 1277 1283 1292 1309 1314 1606 1649Ms119898119911 = 338 (M+ + 1)
7d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
345 464 472 486 502 1212 1234 1239 1246 1256 12631282 1319 1324 1642 1692 Ms119898119911 = 324 (M+ + 1)
7e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1660 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 8H Ar-H) 1300 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 503 513
715 723 1203 1212 1242 1256 1281 1289 1291 12991314 1651 1663 Ms119898119911 = 311 (M+ + 1)
7f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1644 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 126
138 194 399 436 1236 1246 1252 1266 1276 1298 13121335 1365 1667 1683 Ms119898119911 = 311 (M+ + 1)
7g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 205 445 493 505 515 1202 1224
1234 1245 1253 1266 1285 1301 1335 1637 1666 Ms119898119911 = 324 (M+ + 1)
7h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 122 193
442 476 483 512 522 1193 1213 1242 1249 1262 12711304 1313 1323 1611 1651 Ms119898119911 = 352 (M+ + 1)
7i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 184 354 454 463 473 513 1201
1222 1226 1245 1247 1274 1286 1310 1328 1646 1699Ms119898119911 = 338 (M+ + 1)
7j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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International Journal ofPhotoenergy
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Carbohydrate Chemistry
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Journal of
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Advances in
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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
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Journal of
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Analytical ChemistryInternational Journal of
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Quantum Chemistry
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Organic Chemistry International
ElectrochemistryInternational Journal of
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
Organic Chemistry International 3
O
O
O
O
O
OH
HN N
O
O
N
N
HN
O
O
N
N
HN
(1)
(2)
(3)
(4)
(5)
CH3COOHRT10ndash15min
HATUEt3NDMF40ndash65min
HATUEt3NDMF40ndash65min
(2)
(2)
Scheme 1 Synthetic routes to 4andash4e and 5andash5j
The structures of the products have been established onthe basis of their spectral and analytical data An alternateprotocol was attemptedto synthesize 7andash7y by treatment of1 with aniline 6a in acetic acid at 0ndash5∘C for 10ndash15min whichgave 2-(phenylcarbamoyl)benzoic acid 8a18 and subsequentreaction of 8awith diethylamine 2a in the presence of HATUand Et
3N at RT for 20ndash25min in DMF which resulted in the
formation of 2-phenylisoindoline-1 3-dione 9a18
3 Conclusion
In conclusion we have developed novel syntheses of sym-metrical 4andash4e and unsymmetrical 5andash5j and 7andash7y o-phthalic acid diamides This approach presents a simple anduseful synthetic process which requires a few minutes ofreaction time easily available starting materials and straightforward and easy workup procedure Probably this appearsto be the first ever case of facile preparation of symmetricaland unsymmetrical o-phthalic acid diamides The use ofHATU as a coupling agent has been reported in the liter-ature for reactions such as amide bond formation in solidphase synthesis and peptides synthesis However its use inthe preparation of diamides from phthalic anhydride withamines has probably not been reported so far The overallyields of these compounds are very good
4 Materials and Methods
Melting points are uncorrected and were determined in opencapillary tubes in sulphuric acid bath TLC was run on silicagel-G visualization was done using iodine or UV light andIR spectra were recorded using PerkinElmer 1000 instrumentin KBr pellets 1HNMR spectra were recorded in DMSO-d
6
using TMS as internal standard using 400MHz spectrometerMass spectra were recorded on Agilent-LCMS instrumentunder CI conditions and given by 119876 + 1 values only Starting1 2 and 6 were obtained from commercial sources and usedas such
41 Preparation of 3andash3e A mixture of 1a (10mM) 2andash2e (10Mm) and CH
3COOH (20mL) was stirred at RT for
10ndash20min A colourless solid separated out from reactionmixture which was filtered washed with hexane (10mL) anddried The crude product was recrystallized from suitablesolvent to obtain 3andash3e
42 Preparation of 4andash4e amp 5andash5j A mixture of 3andash3e(10mM) 2andash2e (10mM)HATU (10mM) Et
3N (10mM) and
DMF (15mL) was stirred at 0ndash5∘C for 40ndash65min Then ice-cold water (50mL) was added to the reaction mixture Theseparated solid was filtered washed with water (10mL) anddried The product was recrystallized from a suitable solventto obtain 4andash4e and 5andash5j
43 Preparation of 7andash7y A mixture of 3andash3e (10mM)6andash6e (10mM) HATU (10mM) Et
3N (10mM) and DMF
(15mL) was stirred at 0ndash5∘C for 40ndash55min Then ice-cold water (50mL) was added to the reaction mixture Theseparated solid was filtered washed with water (10mL) anddried The product was recrystallized from a suitable solventto obtain 7andash7y
5 Supporting Information
3a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 08 (t 3H ndashCH
3) 120575 12 (t 3H ndashCH
3) 120575 30 (q
2H ndashCH2) 120575 36 (q 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 1300
(s 1H ndashCOOH D2O exchangeable) 1012 (s 1H ndashNH D2Oexchangeable) 13C NMR (DMSO-d
6 400MHz) 123 414
1231 1285 1293 1295 1602 1655 Ms 119898119911 = 222 (M+ +1)
3b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1725 cmminus1 (sharp strong ndashCOndash ofacid group) 1670 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 22 (s 1H ndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
4H Ar-H) 1300 (s 1H ndashCOOH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 494 501 514 519 1241 1255
1273 1285 1612 1648 Ms119898119911 = 235 (M+ + 1)
4 Organic Chemistry International
O
N
O
O
O
O
N
(7)
(8)
(9)
NH-Ar
Ar
OH
(6)(6)
NH-Ar
HN(2)
HN HNC2H5
C2H5
N H CH3 O= HN HN N C2H5 HN N HN(2) (2)
(a) (b) (c) (d) (e)
(6) (a) (b) (c) (d) (e)
HN
Ar = ndashC6H5ndashC6H4ndashCH3(p)ndashC6H4ndashCH3(O)ndashC6H4ndashCl(p)ndashC6H4ndashBr(p)
O
NOH
(3)
+ Et3N
OminusEt3NH
O
O
OminusN
NO
NN
N N
N
O
O
O
O
N
N
NN N
N
NN N
NHO
minus
N
NO
ON
NON
NNN
O NN
minus
N
NN
N
O
O
O
HN H2N-Ar(2) (5)
NNNN
∙∙
∙∙
minusO
NNNN
minus
Ominus
O
N
O H
O
NN
O(4) and (5)
O
N
O
minusH+
O
NNH-Ar
(7) O
+
N +NH-Ar
Ominus
minusH+
N
O
O
O
OHN
(1)CH3COOHRT10ndash15min
(2)
O
O
OHN
(3)
H2N-Ar
HATUEt3NDMF40ndash55min
HATUEt3NDMF20ndash25min
H2N-Ar
CH3COOHRT10ndash15min
minus
Plausible mechanism for 4 5 and 7 from 3
Scheme 2 Synthetic routes to 7andash7y
3c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1730 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 12 (t 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 4H Ar-H) 132 (s 1H ndashCOOH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 494
501 509 519 522 1231 1245 1253 1275 1632 1648 Ms119898119911 = 263 (M+ + 1)
3d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOH groups put together) 1720 cmminus1 (sharp strong ndashCOndashof acid group) 1660 cmminus1 (sharp storng ndashCOndash of amide
Organic Chemistry International 5
Table 3 Characterization data reaction time and yields of 4andash4e and 5andash5j obtained from 3andash3e and 2andash2e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 2a 4a 40ndash45 85 gt2202 3b 2b 4b 40ndash45 85 gt2203 3c 2c 4c 50ndash55 80 gt2204 3d 2d 4d 50ndash55 80 gt2205 3e 2e 4e 40ndash45 80 gt2206 3a 2b 5a 40ndash45 85 gt2207 3a 2c 5b 50ndash55 81 110ndash1128 3a 2d 5c 50ndash55 84 115ndash1189 3a 2e 5d 50ndash55 85 80ndash8210 3b 2a 5a 40ndash45 83 gt22011 3b 2c 5e 50ndash55 84 gt22012 3b 2d 5f 50ndash55 85 gt22013 3b 2e 5g 60ndash65 85 85ndash8714 3c 2a 5b 60ndash65 81 110ndash11215 3c 2b 5e 50ndash55 83 gt22016 3c 2d 5h 50ndash55 85 gt22017 3c 2e 5i 50ndash55 85 90ndash9218 3d 2a 5c 60ndash65 80 115ndash11819 3d 2b 5f 50ndash55 80 gt22020 3d 2c 5h 40ndash45 85 gt22021 3d 2e 5j 40ndash45 83 gt22022 3e 2a 5d 40ndash45 80 80ndash8223 3e 2b 5g 50ndash55 84 85ndash8724 3e 2c 5i 50ndash55 84 90ndash9225 3e 2d 5j 40ndash45 83 gt220= Refers to yields of crude products only
group) 1H-NMR 120575 16 (t 3H ndashCH3) 120575 30 (t 2H ndashCH
2) 120575
32 (t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 4H Ar-H) 131 (s 1H ndashCOOH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 394 551 559 559 552
1261 1275 1283 1295 1602 1658 Ms119898119911 = 249 (M+ + 1)3e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH and
ndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t
2H ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 131
(s 1H ndashCOOH D2O exchangeable) 13C NMR (DMSO-d6
400MHz) 502 506 719 722 1251 1255 1263 1275 16221648 Ms119898119911 = 236 (M+ + 1)
4a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 6HndashCH3 ndashCH
3) 120575 14 (t 6H ndashCH
3 ndashCH
3) 120575 28 (q 4H ndashCH
2
ndashCH2) 120575 32 (q 4H ndashCH
2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13C
NMR (DMSO-d6 400MHz) 129 141 316 367 391 435
1253 1265 1271 1293 1636 1696 Ms119898119911 = 277 (M+ + 1)4b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1685 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22
(s 2H ndashNH ndashNH) 120575 30 (t 8H Four ndashCH2groups) 120575 34
(t 8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 474 486 497 509 515 524 1253
1255 1271 1286 1643 1676 Ms119898119911 = 303 (M+ + 1)4c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1660 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 13 (t 6HndashCH3 ndashCH
3) 120575 28 (q 4H ndashCH
2 ndashCH
2) 120575 32 (t 8H Four
ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80 (m
4H Ar-H) 13C NMR (DMSO-d6 400MHz) 123 161 464
476 487 491 505 514 1233 1245 1281 1289 1646 1686Ms119898119911 = 359 (M+ + 1)
4d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 8H Four ndashCH
2groups) 120575 32 (t
8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 323 334 484 489 497 505 524
553 1253 1256 1283 1299 1652 1693 Ms 119898119911 = 331(M+ + 1)
4e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t 8H
6 Organic Chemistry International
Table 4 Characterization data reaction time and yield of 7andash7y obtained from 3andash3e and 6andash6e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 6a 7a 40ndash45 85 115ndash1182 3b 6a 7b 50ndash55 82 120ndash1233 3c 6a 7c 40ndash45 84 123ndash1254 3d 6a 7d 50ndash55 85 gt2205 3e 6a 7e 50ndash55 80 126ndash1286 3a 6b 7f 40ndash45 83 128ndash1307 3b 6b 7g 40ndash45 82 138ndash1408 3c 6b 7h 50ndash55 82 120ndash1239 3d 6b 7i 50ndash55 85 gt22010 3e 6b 7j 40ndash45 80 122ndash12411 3a 6c 7k 50ndash55 82 120ndash12412 3b 6c 7l 40ndash45 85 130ndash13213 3c 6c 7m 50ndash55 85 170ndash17414 3d 6c 7n 50ndash55 80 gt22015 3e 6c 7o 40ndash45 80 140ndash14316 3a 6d 7p 40ndash45 80 125ndash12817 3b 6d 7q 50ndash55 82 135ndash13718 3c 6d 7r 50ndash55 82 180ndash18319 3d 6d 7s 40ndash45 80 gt22020 3e 6d 7t 40ndash45 85 142ndash14521 3a 6e 7u 40ndash45 84 128ndash13022 3b 6e 7v 40ndash45 85 133ndash13523 3c 6e 7w 50ndash55 80 190ndash19224 3d 6e 7x 50ndash55 82 gt22025 3e 6e 7y 40ndash45 84 145ndash148= Refers to yields of crude products only
Four ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80
(m 4H Ar-H) 13C NMR (DMSO-d6 400MHz) 493 499
507 528 559 568 1254 1263 1274 1289 1642 1673 Ms119898119911 = 305 (M+ + 1)
5a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1660 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 22 (s 1H ndashNH) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 129 317 435 446 511 525 1231 1243 1283
1296 1617 1655 Ms119898119911 = 290 (M+ + 1)5b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 14 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2)
120575 30 (t 4H ndashCH2 ndashCH
2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34
(q 2H ndashCH2) 120575 36 (q 2H ndashCH
2 ndashCH
2) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 129 136 315 445
456 486 541 555 1236 1253 1283 1296 1627 1654 Ms119898119911 = 318 (M+ + 1)
5c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 18 (t 3H ndashCH
3) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 139 327 415 446 455 531 545 1223 1253
1292 1299 1647 1664 Ms119898119911 = 304 (M+ + 1)5d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 4H ndashCH
2 ndashCH
2) 120575 32 (t 4H ndash
CH2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q 2H ndashCH
2 ndashCH
2)
70ndash80 (m 4H Ar-H) 13CNMR (DMSO-d6 400MHz) 132
334 443 452 501 524 1242 1235 1254 1257 1603 1656Ms119898119911 = 291 (M+ + 1)
5e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 22 (q 2H ndashCH
2) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 124 294 302 317 334 343 425
436 502 512 1241 1252 1273 1293 1603 1642Ms119898119911 =331 (M+ + 1)
5f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1
Organic Chemistry International 7
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 284 314 325 333 354 414 424 514 5231252 1261 1283 1292 1616 1651 Ms119898119911 = 317 (M+ + 1)
5g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 28ndash36 (t 16H eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 301 313 335 342
426 438 501 514 1232 1251 1282 1293 1603 1653 Ms119898119911 = 304 (M+ + 1)
5h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 18 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 132 286 295 322 337 345 354
435 445 535 546 1255 1264 1269 1295 1613 1659 Ms119898119911 = 345 (M+ + 1)
5i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 132 294 312 322 332 345 427 448 509 5191243 1259 1278 1290 1607 1689 Ms119898119911 = 332 (M+ + 1)
5j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 28ndash36 (t 16H Eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H)13CNMR (DMSO-d6 400MHz) 284 332 347 354
393 445 476 532 552 1271 1282 1293 1299 1633 1694Ms119898119911 = 318 (M+ + 1)
7a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t6H ndashCH
3 ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34 (q 2H ndashCH
2)
70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 122 134 379 425 1234
1262 1278 1281 1285 1303 1341 1374 1391 1658 1692Ms119898119911 = 297 (M+ + 1)
7b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H
ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 104 (s 1H
ndashNH D2O exchangeable)13C NMR (DMSO-d6 400MHz)
493 503 515 513 1243 1245 1255 1264 1273 1285 12951299 1315 1632 1645 Ms119898119911 = 310 (M+ + 1)
7c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 26 (q 2H ndashCH
2) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 126 445 473 485 505 513 1203
1227 1254 1263 1277 1283 1292 1309 1314 1606 1649Ms119898119911 = 338 (M+ + 1)
7d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
345 464 472 486 502 1212 1234 1239 1246 1256 12631282 1319 1324 1642 1692 Ms119898119911 = 324 (M+ + 1)
7e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1660 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 8H Ar-H) 1300 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 503 513
715 723 1203 1212 1242 1256 1281 1289 1291 12991314 1651 1663 Ms119898119911 = 311 (M+ + 1)
7f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1644 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 126
138 194 399 436 1236 1246 1252 1266 1276 1298 13121335 1365 1667 1683 Ms119898119911 = 311 (M+ + 1)
7g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 205 445 493 505 515 1202 1224
1234 1245 1253 1266 1285 1301 1335 1637 1666 Ms119898119911 = 324 (M+ + 1)
7h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 122 193
442 476 483 512 522 1193 1213 1242 1249 1262 12711304 1313 1323 1611 1651 Ms119898119911 = 352 (M+ + 1)
7i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 184 354 454 463 473 513 1201
1222 1226 1245 1247 1274 1286 1310 1328 1646 1699Ms119898119911 = 338 (M+ + 1)
7j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Carbohydrate Chemistry
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Journal of
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Advances in
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Analytical Methods in Chemistry
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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
SpectroscopyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
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Journal of
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Analytical ChemistryInternational Journal of
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Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
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CatalystsJournal of
4 Organic Chemistry International
O
N
O
O
O
O
N
(7)
(8)
(9)
NH-Ar
Ar
OH
(6)(6)
NH-Ar
HN(2)
HN HNC2H5
C2H5
N H CH3 O= HN HN N C2H5 HN N HN(2) (2)
(a) (b) (c) (d) (e)
(6) (a) (b) (c) (d) (e)
HN
Ar = ndashC6H5ndashC6H4ndashCH3(p)ndashC6H4ndashCH3(O)ndashC6H4ndashCl(p)ndashC6H4ndashBr(p)
O
NOH
(3)
+ Et3N
OminusEt3NH
O
O
OminusN
NO
NN
N N
N
O
O
O
O
N
N
NN N
N
NN N
NHO
minus
N
NO
ON
NON
NNN
O NN
minus
N
NN
N
O
O
O
HN H2N-Ar(2) (5)
NNNN
∙∙
∙∙
minusO
NNNN
minus
Ominus
O
N
O H
O
NN
O(4) and (5)
O
N
O
minusH+
O
NNH-Ar
(7) O
+
N +NH-Ar
Ominus
minusH+
N
O
O
O
OHN
(1)CH3COOHRT10ndash15min
(2)
O
O
OHN
(3)
H2N-Ar
HATUEt3NDMF40ndash55min
HATUEt3NDMF20ndash25min
H2N-Ar
CH3COOHRT10ndash15min
minus
Plausible mechanism for 4 5 and 7 from 3
Scheme 2 Synthetic routes to 7andash7y
3c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOHgroups put together) 1730 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 12 (t 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 4H Ar-H) 132 (s 1H ndashCOOH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 494
501 509 519 522 1231 1245 1253 1275 1632 1648 Ms119898119911 = 263 (M+ + 1)
3d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH andndashOH groups put together) 1720 cmminus1 (sharp strong ndashCOndashof acid group) 1660 cmminus1 (sharp storng ndashCOndash of amide
Organic Chemistry International 5
Table 3 Characterization data reaction time and yields of 4andash4e and 5andash5j obtained from 3andash3e and 2andash2e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 2a 4a 40ndash45 85 gt2202 3b 2b 4b 40ndash45 85 gt2203 3c 2c 4c 50ndash55 80 gt2204 3d 2d 4d 50ndash55 80 gt2205 3e 2e 4e 40ndash45 80 gt2206 3a 2b 5a 40ndash45 85 gt2207 3a 2c 5b 50ndash55 81 110ndash1128 3a 2d 5c 50ndash55 84 115ndash1189 3a 2e 5d 50ndash55 85 80ndash8210 3b 2a 5a 40ndash45 83 gt22011 3b 2c 5e 50ndash55 84 gt22012 3b 2d 5f 50ndash55 85 gt22013 3b 2e 5g 60ndash65 85 85ndash8714 3c 2a 5b 60ndash65 81 110ndash11215 3c 2b 5e 50ndash55 83 gt22016 3c 2d 5h 50ndash55 85 gt22017 3c 2e 5i 50ndash55 85 90ndash9218 3d 2a 5c 60ndash65 80 115ndash11819 3d 2b 5f 50ndash55 80 gt22020 3d 2c 5h 40ndash45 85 gt22021 3d 2e 5j 40ndash45 83 gt22022 3e 2a 5d 40ndash45 80 80ndash8223 3e 2b 5g 50ndash55 84 85ndash8724 3e 2c 5i 50ndash55 84 90ndash9225 3e 2d 5j 40ndash45 83 gt220= Refers to yields of crude products only
group) 1H-NMR 120575 16 (t 3H ndashCH3) 120575 30 (t 2H ndashCH
2) 120575
32 (t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 4H Ar-H) 131 (s 1H ndashCOOH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 394 551 559 559 552
1261 1275 1283 1295 1602 1658 Ms119898119911 = 249 (M+ + 1)3e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH and
ndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t
2H ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 131
(s 1H ndashCOOH D2O exchangeable) 13C NMR (DMSO-d6
400MHz) 502 506 719 722 1251 1255 1263 1275 16221648 Ms119898119911 = 236 (M+ + 1)
4a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 6HndashCH3 ndashCH
3) 120575 14 (t 6H ndashCH
3 ndashCH
3) 120575 28 (q 4H ndashCH
2
ndashCH2) 120575 32 (q 4H ndashCH
2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13C
NMR (DMSO-d6 400MHz) 129 141 316 367 391 435
1253 1265 1271 1293 1636 1696 Ms119898119911 = 277 (M+ + 1)4b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1685 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22
(s 2H ndashNH ndashNH) 120575 30 (t 8H Four ndashCH2groups) 120575 34
(t 8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 474 486 497 509 515 524 1253
1255 1271 1286 1643 1676 Ms119898119911 = 303 (M+ + 1)4c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1660 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 13 (t 6HndashCH3 ndashCH
3) 120575 28 (q 4H ndashCH
2 ndashCH
2) 120575 32 (t 8H Four
ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80 (m
4H Ar-H) 13C NMR (DMSO-d6 400MHz) 123 161 464
476 487 491 505 514 1233 1245 1281 1289 1646 1686Ms119898119911 = 359 (M+ + 1)
4d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 8H Four ndashCH
2groups) 120575 32 (t
8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 323 334 484 489 497 505 524
553 1253 1256 1283 1299 1652 1693 Ms 119898119911 = 331(M+ + 1)
4e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t 8H
6 Organic Chemistry International
Table 4 Characterization data reaction time and yield of 7andash7y obtained from 3andash3e and 6andash6e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 6a 7a 40ndash45 85 115ndash1182 3b 6a 7b 50ndash55 82 120ndash1233 3c 6a 7c 40ndash45 84 123ndash1254 3d 6a 7d 50ndash55 85 gt2205 3e 6a 7e 50ndash55 80 126ndash1286 3a 6b 7f 40ndash45 83 128ndash1307 3b 6b 7g 40ndash45 82 138ndash1408 3c 6b 7h 50ndash55 82 120ndash1239 3d 6b 7i 50ndash55 85 gt22010 3e 6b 7j 40ndash45 80 122ndash12411 3a 6c 7k 50ndash55 82 120ndash12412 3b 6c 7l 40ndash45 85 130ndash13213 3c 6c 7m 50ndash55 85 170ndash17414 3d 6c 7n 50ndash55 80 gt22015 3e 6c 7o 40ndash45 80 140ndash14316 3a 6d 7p 40ndash45 80 125ndash12817 3b 6d 7q 50ndash55 82 135ndash13718 3c 6d 7r 50ndash55 82 180ndash18319 3d 6d 7s 40ndash45 80 gt22020 3e 6d 7t 40ndash45 85 142ndash14521 3a 6e 7u 40ndash45 84 128ndash13022 3b 6e 7v 40ndash45 85 133ndash13523 3c 6e 7w 50ndash55 80 190ndash19224 3d 6e 7x 50ndash55 82 gt22025 3e 6e 7y 40ndash45 84 145ndash148= Refers to yields of crude products only
Four ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80
(m 4H Ar-H) 13C NMR (DMSO-d6 400MHz) 493 499
507 528 559 568 1254 1263 1274 1289 1642 1673 Ms119898119911 = 305 (M+ + 1)
5a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1660 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 22 (s 1H ndashNH) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 129 317 435 446 511 525 1231 1243 1283
1296 1617 1655 Ms119898119911 = 290 (M+ + 1)5b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 14 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2)
120575 30 (t 4H ndashCH2 ndashCH
2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34
(q 2H ndashCH2) 120575 36 (q 2H ndashCH
2 ndashCH
2) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 129 136 315 445
456 486 541 555 1236 1253 1283 1296 1627 1654 Ms119898119911 = 318 (M+ + 1)
5c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 18 (t 3H ndashCH
3) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 139 327 415 446 455 531 545 1223 1253
1292 1299 1647 1664 Ms119898119911 = 304 (M+ + 1)5d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 4H ndashCH
2 ndashCH
2) 120575 32 (t 4H ndash
CH2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q 2H ndashCH
2 ndashCH
2)
70ndash80 (m 4H Ar-H) 13CNMR (DMSO-d6 400MHz) 132
334 443 452 501 524 1242 1235 1254 1257 1603 1656Ms119898119911 = 291 (M+ + 1)
5e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 22 (q 2H ndashCH
2) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 124 294 302 317 334 343 425
436 502 512 1241 1252 1273 1293 1603 1642Ms119898119911 =331 (M+ + 1)
5f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1
Organic Chemistry International 7
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 284 314 325 333 354 414 424 514 5231252 1261 1283 1292 1616 1651 Ms119898119911 = 317 (M+ + 1)
5g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 28ndash36 (t 16H eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 301 313 335 342
426 438 501 514 1232 1251 1282 1293 1603 1653 Ms119898119911 = 304 (M+ + 1)
5h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 18 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 132 286 295 322 337 345 354
435 445 535 546 1255 1264 1269 1295 1613 1659 Ms119898119911 = 345 (M+ + 1)
5i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 132 294 312 322 332 345 427 448 509 5191243 1259 1278 1290 1607 1689 Ms119898119911 = 332 (M+ + 1)
5j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 28ndash36 (t 16H Eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H)13CNMR (DMSO-d6 400MHz) 284 332 347 354
393 445 476 532 552 1271 1282 1293 1299 1633 1694Ms119898119911 = 318 (M+ + 1)
7a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t6H ndashCH
3 ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34 (q 2H ndashCH
2)
70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 122 134 379 425 1234
1262 1278 1281 1285 1303 1341 1374 1391 1658 1692Ms119898119911 = 297 (M+ + 1)
7b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H
ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 104 (s 1H
ndashNH D2O exchangeable)13C NMR (DMSO-d6 400MHz)
493 503 515 513 1243 1245 1255 1264 1273 1285 12951299 1315 1632 1645 Ms119898119911 = 310 (M+ + 1)
7c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 26 (q 2H ndashCH
2) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 126 445 473 485 505 513 1203
1227 1254 1263 1277 1283 1292 1309 1314 1606 1649Ms119898119911 = 338 (M+ + 1)
7d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
345 464 472 486 502 1212 1234 1239 1246 1256 12631282 1319 1324 1642 1692 Ms119898119911 = 324 (M+ + 1)
7e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1660 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 8H Ar-H) 1300 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 503 513
715 723 1203 1212 1242 1256 1281 1289 1291 12991314 1651 1663 Ms119898119911 = 311 (M+ + 1)
7f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1644 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 126
138 194 399 436 1236 1246 1252 1266 1276 1298 13121335 1365 1667 1683 Ms119898119911 = 311 (M+ + 1)
7g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 205 445 493 505 515 1202 1224
1234 1245 1253 1266 1285 1301 1335 1637 1666 Ms119898119911 = 324 (M+ + 1)
7h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 122 193
442 476 483 512 522 1193 1213 1242 1249 1262 12711304 1313 1323 1611 1651 Ms119898119911 = 352 (M+ + 1)
7i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 184 354 454 463 473 513 1201
1222 1226 1245 1247 1274 1286 1310 1328 1646 1699Ms119898119911 = 338 (M+ + 1)
7j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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CatalystsJournal of
Organic Chemistry International 5
Table 3 Characterization data reaction time and yields of 4andash4e and 5andash5j obtained from 3andash3e and 2andash2e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 2a 4a 40ndash45 85 gt2202 3b 2b 4b 40ndash45 85 gt2203 3c 2c 4c 50ndash55 80 gt2204 3d 2d 4d 50ndash55 80 gt2205 3e 2e 4e 40ndash45 80 gt2206 3a 2b 5a 40ndash45 85 gt2207 3a 2c 5b 50ndash55 81 110ndash1128 3a 2d 5c 50ndash55 84 115ndash1189 3a 2e 5d 50ndash55 85 80ndash8210 3b 2a 5a 40ndash45 83 gt22011 3b 2c 5e 50ndash55 84 gt22012 3b 2d 5f 50ndash55 85 gt22013 3b 2e 5g 60ndash65 85 85ndash8714 3c 2a 5b 60ndash65 81 110ndash11215 3c 2b 5e 50ndash55 83 gt22016 3c 2d 5h 50ndash55 85 gt22017 3c 2e 5i 50ndash55 85 90ndash9218 3d 2a 5c 60ndash65 80 115ndash11819 3d 2b 5f 50ndash55 80 gt22020 3d 2c 5h 40ndash45 85 gt22021 3d 2e 5j 40ndash45 83 gt22022 3e 2a 5d 40ndash45 80 80ndash8223 3e 2b 5g 50ndash55 84 85ndash8724 3e 2c 5i 50ndash55 84 90ndash9225 3e 2d 5j 40ndash45 83 gt220= Refers to yields of crude products only
group) 1H-NMR 120575 16 (t 3H ndashCH3) 120575 30 (t 2H ndashCH
2) 120575
32 (t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 4H Ar-H) 131 (s 1H ndashCOOH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 394 551 559 559 552
1261 1275 1283 1295 1602 1658 Ms119898119911 = 249 (M+ + 1)3e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNH and
ndashOHgroups put together) 1720 cmminus1 (sharp strong ndashCOndashofacid group) 1655 cmminus1 (sharp storng ndashCOndashof amide group)1H-NMR 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t
2H ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 4H Ar-H) 131
(s 1H ndashCOOH D2O exchangeable) 13C NMR (DMSO-d6
400MHz) 502 506 719 722 1251 1255 1263 1275 16221648 Ms119898119911 = 236 (M+ + 1)
4a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 6HndashCH3 ndashCH
3) 120575 14 (t 6H ndashCH
3 ndashCH
3) 120575 28 (q 4H ndashCH
2
ndashCH2) 120575 32 (q 4H ndashCH
2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13C
NMR (DMSO-d6 400MHz) 129 141 316 367 391 435
1253 1265 1271 1293 1636 1696 Ms119898119911 = 277 (M+ + 1)4b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1685 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22
(s 2H ndashNH ndashNH) 120575 30 (t 8H Four ndashCH2groups) 120575 34
(t 8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 474 486 497 509 515 524 1253
1255 1271 1286 1643 1676 Ms119898119911 = 303 (M+ + 1)4c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1660 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 13 (t 6HndashCH3 ndashCH
3) 120575 28 (q 4H ndashCH
2 ndashCH
2) 120575 32 (t 8H Four
ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80 (m
4H Ar-H) 13C NMR (DMSO-d6 400MHz) 123 161 464
476 487 491 505 514 1233 1245 1281 1289 1646 1686Ms119898119911 = 359 (M+ + 1)
4d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 8H Four ndashCH
2groups) 120575 32 (t
8H Four ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 323 334 484 489 497 505 524
553 1253 1256 1283 1299 1652 1693 Ms 119898119911 = 331(M+ + 1)
4e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t 8H
6 Organic Chemistry International
Table 4 Characterization data reaction time and yield of 7andash7y obtained from 3andash3e and 6andash6e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 6a 7a 40ndash45 85 115ndash1182 3b 6a 7b 50ndash55 82 120ndash1233 3c 6a 7c 40ndash45 84 123ndash1254 3d 6a 7d 50ndash55 85 gt2205 3e 6a 7e 50ndash55 80 126ndash1286 3a 6b 7f 40ndash45 83 128ndash1307 3b 6b 7g 40ndash45 82 138ndash1408 3c 6b 7h 50ndash55 82 120ndash1239 3d 6b 7i 50ndash55 85 gt22010 3e 6b 7j 40ndash45 80 122ndash12411 3a 6c 7k 50ndash55 82 120ndash12412 3b 6c 7l 40ndash45 85 130ndash13213 3c 6c 7m 50ndash55 85 170ndash17414 3d 6c 7n 50ndash55 80 gt22015 3e 6c 7o 40ndash45 80 140ndash14316 3a 6d 7p 40ndash45 80 125ndash12817 3b 6d 7q 50ndash55 82 135ndash13718 3c 6d 7r 50ndash55 82 180ndash18319 3d 6d 7s 40ndash45 80 gt22020 3e 6d 7t 40ndash45 85 142ndash14521 3a 6e 7u 40ndash45 84 128ndash13022 3b 6e 7v 40ndash45 85 133ndash13523 3c 6e 7w 50ndash55 80 190ndash19224 3d 6e 7x 50ndash55 82 gt22025 3e 6e 7y 40ndash45 84 145ndash148= Refers to yields of crude products only
Four ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80
(m 4H Ar-H) 13C NMR (DMSO-d6 400MHz) 493 499
507 528 559 568 1254 1263 1274 1289 1642 1673 Ms119898119911 = 305 (M+ + 1)
5a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1660 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 22 (s 1H ndashNH) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 129 317 435 446 511 525 1231 1243 1283
1296 1617 1655 Ms119898119911 = 290 (M+ + 1)5b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 14 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2)
120575 30 (t 4H ndashCH2 ndashCH
2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34
(q 2H ndashCH2) 120575 36 (q 2H ndashCH
2 ndashCH
2) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 129 136 315 445
456 486 541 555 1236 1253 1283 1296 1627 1654 Ms119898119911 = 318 (M+ + 1)
5c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 18 (t 3H ndashCH
3) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 139 327 415 446 455 531 545 1223 1253
1292 1299 1647 1664 Ms119898119911 = 304 (M+ + 1)5d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 4H ndashCH
2 ndashCH
2) 120575 32 (t 4H ndash
CH2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q 2H ndashCH
2 ndashCH
2)
70ndash80 (m 4H Ar-H) 13CNMR (DMSO-d6 400MHz) 132
334 443 452 501 524 1242 1235 1254 1257 1603 1656Ms119898119911 = 291 (M+ + 1)
5e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 22 (q 2H ndashCH
2) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 124 294 302 317 334 343 425
436 502 512 1241 1252 1273 1293 1603 1642Ms119898119911 =331 (M+ + 1)
5f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1
Organic Chemistry International 7
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 284 314 325 333 354 414 424 514 5231252 1261 1283 1292 1616 1651 Ms119898119911 = 317 (M+ + 1)
5g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 28ndash36 (t 16H eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 301 313 335 342
426 438 501 514 1232 1251 1282 1293 1603 1653 Ms119898119911 = 304 (M+ + 1)
5h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 18 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 132 286 295 322 337 345 354
435 445 535 546 1255 1264 1269 1295 1613 1659 Ms119898119911 = 345 (M+ + 1)
5i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 132 294 312 322 332 345 427 448 509 5191243 1259 1278 1290 1607 1689 Ms119898119911 = 332 (M+ + 1)
5j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 28ndash36 (t 16H Eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H)13CNMR (DMSO-d6 400MHz) 284 332 347 354
393 445 476 532 552 1271 1282 1293 1299 1633 1694Ms119898119911 = 318 (M+ + 1)
7a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t6H ndashCH
3 ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34 (q 2H ndashCH
2)
70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 122 134 379 425 1234
1262 1278 1281 1285 1303 1341 1374 1391 1658 1692Ms119898119911 = 297 (M+ + 1)
7b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H
ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 104 (s 1H
ndashNH D2O exchangeable)13C NMR (DMSO-d6 400MHz)
493 503 515 513 1243 1245 1255 1264 1273 1285 12951299 1315 1632 1645 Ms119898119911 = 310 (M+ + 1)
7c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 26 (q 2H ndashCH
2) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 126 445 473 485 505 513 1203
1227 1254 1263 1277 1283 1292 1309 1314 1606 1649Ms119898119911 = 338 (M+ + 1)
7d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
345 464 472 486 502 1212 1234 1239 1246 1256 12631282 1319 1324 1642 1692 Ms119898119911 = 324 (M+ + 1)
7e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1660 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 8H Ar-H) 1300 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 503 513
715 723 1203 1212 1242 1256 1281 1289 1291 12991314 1651 1663 Ms119898119911 = 311 (M+ + 1)
7f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1644 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 126
138 194 399 436 1236 1246 1252 1266 1276 1298 13121335 1365 1667 1683 Ms119898119911 = 311 (M+ + 1)
7g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 205 445 493 505 515 1202 1224
1234 1245 1253 1266 1285 1301 1335 1637 1666 Ms119898119911 = 324 (M+ + 1)
7h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 122 193
442 476 483 512 522 1193 1213 1242 1249 1262 12711304 1313 1323 1611 1651 Ms119898119911 = 352 (M+ + 1)
7i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 184 354 454 463 473 513 1201
1222 1226 1245 1247 1274 1286 1310 1328 1646 1699Ms119898119911 = 338 (M+ + 1)
7j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Analytical ChemistryInternational Journal of
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Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
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CatalystsJournal of
6 Organic Chemistry International
Table 4 Characterization data reaction time and yield of 7andash7y obtained from 3andash3e and 6andash6e
Entry Starting material used Product obtained Time (min) Yield = MP (∘C)1 3a 6a 7a 40ndash45 85 115ndash1182 3b 6a 7b 50ndash55 82 120ndash1233 3c 6a 7c 40ndash45 84 123ndash1254 3d 6a 7d 50ndash55 85 gt2205 3e 6a 7e 50ndash55 80 126ndash1286 3a 6b 7f 40ndash45 83 128ndash1307 3b 6b 7g 40ndash45 82 138ndash1408 3c 6b 7h 50ndash55 82 120ndash1239 3d 6b 7i 50ndash55 85 gt22010 3e 6b 7j 40ndash45 80 122ndash12411 3a 6c 7k 50ndash55 82 120ndash12412 3b 6c 7l 40ndash45 85 130ndash13213 3c 6c 7m 50ndash55 85 170ndash17414 3d 6c 7n 50ndash55 80 gt22015 3e 6c 7o 40ndash45 80 140ndash14316 3a 6d 7p 40ndash45 80 125ndash12817 3b 6d 7q 50ndash55 82 135ndash13718 3c 6d 7r 50ndash55 82 180ndash18319 3d 6d 7s 40ndash45 80 gt22020 3e 6d 7t 40ndash45 85 142ndash14521 3a 6e 7u 40ndash45 84 128ndash13022 3b 6e 7v 40ndash45 85 133ndash13523 3c 6e 7w 50ndash55 80 190ndash19224 3d 6e 7x 50ndash55 82 gt22025 3e 6e 7y 40ndash45 84 145ndash148= Refers to yields of crude products only
Four ndashCH2groups) 120575 32 (t 8H Four ndashCH
2groups) 70ndash80
(m 4H Ar-H) 13C NMR (DMSO-d6 400MHz) 493 499
507 528 559 568 1254 1263 1274 1289 1642 1673 Ms119898119911 = 305 (M+ + 1)
5a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1660 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 22 (s 1H ndashNH) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 129 317 435 446 511 525 1231 1243 1283
1296 1617 1655 Ms119898119911 = 290 (M+ + 1)5b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 14 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2)
120575 30 (t 4H ndashCH2 ndashCH
2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34
(q 2H ndashCH2) 120575 36 (q 2H ndashCH
2 ndashCH
2) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 129 136 315 445
456 486 541 555 1236 1253 1283 1296 1627 1654 Ms119898119911 = 318 (M+ + 1)
5c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 18 (t 3H ndashCH
3) 120575 30 (t 4H ndashCH
2 ndash
CH2) 120575 32 (t 4H ndashCH
2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q
2H ndashCH2 ndashCH
2) 70ndash80 (m 4H Ar-H) 13CNMR (DMSO-
d6 400MHz) 139 327 415 446 455 531 545 1223 1253
1292 1299 1647 1664 Ms119898119911 = 304 (M+ + 1)5d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)
1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10ndash12 (t6H ndashCH
3 ndashCH
3) 120575 30 (t 4H ndashCH
2 ndashCH
2) 120575 32 (t 4H ndash
CH2 ndashCH
2) 120575 34 (q 2H ndashCH
2) 120575 36 (q 2H ndashCH
2 ndashCH
2)
70ndash80 (m 4H Ar-H) 13CNMR (DMSO-d6 400MHz) 132
334 443 452 501 524 1242 1235 1254 1257 1603 1656Ms119898119911 = 291 (M+ + 1)
5e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1665 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 22 (q 2H ndashCH
2) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 124 294 302 317 334 343 425
436 502 512 1241 1252 1273 1293 1603 1642Ms119898119911 =331 (M+ + 1)
5f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1
Organic Chemistry International 7
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 284 314 325 333 354 414 424 514 5231252 1261 1283 1292 1616 1651 Ms119898119911 = 317 (M+ + 1)
5g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 28ndash36 (t 16H eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 301 313 335 342
426 438 501 514 1232 1251 1282 1293 1603 1653 Ms119898119911 = 304 (M+ + 1)
5h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 18 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 132 286 295 322 337 345 354
435 445 535 546 1255 1264 1269 1295 1613 1659 Ms119898119911 = 345 (M+ + 1)
5i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 132 294 312 322 332 345 427 448 509 5191243 1259 1278 1290 1607 1689 Ms119898119911 = 332 (M+ + 1)
5j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 28ndash36 (t 16H Eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H)13CNMR (DMSO-d6 400MHz) 284 332 347 354
393 445 476 532 552 1271 1282 1293 1299 1633 1694Ms119898119911 = 318 (M+ + 1)
7a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t6H ndashCH
3 ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34 (q 2H ndashCH
2)
70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 122 134 379 425 1234
1262 1278 1281 1285 1303 1341 1374 1391 1658 1692Ms119898119911 = 297 (M+ + 1)
7b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H
ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 104 (s 1H
ndashNH D2O exchangeable)13C NMR (DMSO-d6 400MHz)
493 503 515 513 1243 1245 1255 1264 1273 1285 12951299 1315 1632 1645 Ms119898119911 = 310 (M+ + 1)
7c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 26 (q 2H ndashCH
2) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 126 445 473 485 505 513 1203
1227 1254 1263 1277 1283 1292 1309 1314 1606 1649Ms119898119911 = 338 (M+ + 1)
7d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
345 464 472 486 502 1212 1234 1239 1246 1256 12631282 1319 1324 1642 1692 Ms119898119911 = 324 (M+ + 1)
7e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1660 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 8H Ar-H) 1300 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 503 513
715 723 1203 1212 1242 1256 1281 1289 1291 12991314 1651 1663 Ms119898119911 = 311 (M+ + 1)
7f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1644 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 126
138 194 399 436 1236 1246 1252 1266 1276 1298 13121335 1365 1667 1683 Ms119898119911 = 311 (M+ + 1)
7g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 205 445 493 505 515 1202 1224
1234 1245 1253 1266 1285 1301 1335 1637 1666 Ms119898119911 = 324 (M+ + 1)
7h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 122 193
442 476 483 512 522 1193 1213 1242 1249 1262 12711304 1313 1323 1611 1651 Ms119898119911 = 352 (M+ + 1)
7i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 184 354 454 463 473 513 1201
1222 1226 1245 1247 1274 1286 1310 1328 1646 1699Ms119898119911 = 338 (M+ + 1)
7j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Carbohydrate Chemistry
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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Quantum Chemistry
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Organic Chemistry International
ElectrochemistryInternational Journal of
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CatalystsJournal of
Organic Chemistry International 7
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 22 (s 1H ndashNH) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 284 314 325 333 354 414 424 514 5231252 1261 1283 1292 1616 1651 Ms119898119911 = 317 (M+ + 1)
5g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 28ndash36 (t 16H eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H) 13CNMR (DMSO-d6 400MHz) 301 313 335 342
426 438 501 514 1232 1251 1282 1293 1603 1653 Ms119898119911 = 304 (M+ + 1)
5h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 18 (t 3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t
16H eight ndashCH2groups) 70ndash80 (m 4H Ar-H) 13C NMR
(DMSO-d6 400MHz) 132 286 295 322 337 345 354
435 445 535 546 1255 1264 1269 1295 1613 1659 Ms119898119911 = 345 (M+ + 1)
5i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of amide group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t3H ndashCH
3) 120575 22 (q 2H ndashCH
2) 120575 28ndash36 (t 16H eight ndash
CH2groups) 70ndash80 (m 4H Ar-H) 13C NMR (DMSO-d
6
400MHz) 132 294 312 322 332 345 427 448 509 5191243 1259 1278 1290 1607 1689 Ms119898119911 = 332 (M+ + 1)
5j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of amide group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 28ndash36 (t 16H Eight ndashCH
2groups) 70ndash80 (m 4H
Ar-H)13CNMR (DMSO-d6 400MHz) 284 332 347 354
393 445 476 532 552 1271 1282 1293 1299 1633 1694Ms119898119911 = 318 (M+ + 1)
7a IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t6H ndashCH
3 ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34 (q 2H ndashCH
2)
70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 122 134 379 425 1234
1262 1278 1281 1285 1303 1341 1374 1391 1658 1692Ms119898119911 = 297 (M+ + 1)
7b IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H
ndashCH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 104 (s 1H
ndashNH D2O exchangeable)13C NMR (DMSO-d6 400MHz)
493 503 515 513 1243 1245 1255 1264 1273 1285 12951299 1315 1632 1645 Ms119898119911 = 310 (M+ + 1)
7c IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 26 (q 2H ndashCH
2) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 126 445 473 485 505 513 1203
1227 1254 1263 1277 1283 1292 1309 1314 1606 1649Ms119898119911 = 338 (M+ + 1)
7d IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
345 464 472 486 502 1212 1234 1239 1246 1256 12631282 1319 1324 1642 1692 Ms119898119911 = 324 (M+ + 1)
7e IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1660 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 30 (t2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38 (t
2H ndashCH2) 70ndash80 (m 8H Ar-H) 1300 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 503 513
715 723 1203 1212 1242 1256 1281 1289 1291 12991314 1651 1663 Ms119898119911 = 311 (M+ + 1)
7f IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1644 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 126
138 194 399 436 1236 1246 1252 1266 1276 1298 13121335 1365 1667 1683 Ms119898119911 = 311 (M+ + 1)
7g IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 205 445 493 505 515 1202 1224
1234 1245 1253 1266 1285 1301 1335 1637 1666 Ms119898119911 = 324 (M+ + 1)
7h IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 122 193
442 476 483 512 522 1193 1213 1242 1249 1262 12711304 1313 1323 1611 1651 Ms119898119911 = 352 (M+ + 1)
7i IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 184 354 454 463 473 513 1201
1222 1226 1245 1247 1274 1286 1310 1328 1646 1699Ms119898119911 = 338 (M+ + 1)
7j IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Quantum Chemistry
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Organic Chemistry International
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CatalystsJournal of
8 Organic Chemistry International
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
179 512 520 702 724 1212 1224 1253 1260 1269 12701296 1301 1315 1604 1667 Ms119898119911 = 325 (M+ + 1)
7k IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1645 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 11 (t 6HndashCH3 ndashCH
3) 120575 26 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575
34 (q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH
D2O exchangeable) 13C NMR (DMSO-d6 400MHz) 124
135 196 409 435 1246 1256 1267 1286 1294 1306 13121365 1355 1669 1687 Ms119898119911 = 311 (M+ + 1)
7l IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s1H ndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 34
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 8H Ar-H) 106 (s 1H ndashNH D2O exchangeable) 13CNMR (DMSO-d
6 400MHz) 195 434 455 525 534 1193
1234 1239 1249 1255 1276 1287 1302 1325 1613 1665Ms119898119911 = 324 (M+ + 1)
7m IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1695 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 14 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 1123 182
421 434 452 508 513 1195 1204 1245 1269 1274 12611306 1313 1326 1601 1656 Ms119898119911 = 352 (M+ + 1)
7n IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1683 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 183 363 435 452 462 502 1212
1211 1224 1244 1256 1263 1272 1300 1314 1626 1668Ms119898119911 = 338 (M+ + 1)
7o IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1685 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
185 501 516 735 743 1192 1202 1212 1221 1234 12411253 1273 1283 1635 1674 Ms119898119911 = 325 (M+ + 1)
7p IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1670 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 8H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 144
329 405 1214 1258 1268 1291 1303 1314 1346 13841399 1636 1699 Ms119898119911 = 331 (M+ + 1)
7q IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1684 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 104 (s 1H ndashNH D2O exchangeable) 13C NMR(DMSO-d
6 400MHz) 445 449 532 542 1196 1205 1219
1229 1275 1285 1296 1302 1313 1624 1642 Ms 119898119911 =344 (M+ + 1)
7r IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1650 cmminus1 (sharp strong ndashCOndash of acid group) 1640 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 8H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 128 442
454 462 518 524 1196 1215 1245 1256 1273 1256 13021324 1357 1607 1659 Ms119898119911 = 372 (M+ + 1)
7s IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1640 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
8H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 383 456 462 475 506 1232 1266
1273 1283 1291 1299 1302 1314 1324 1603 1664 Ms119898119911 = 358 (M+ + 1)
7t IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 8H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
481 506 725 731 1195 1206 1223 1229 1235 1243 12571263 1293 1657 1694 Ms119898119911 = 345 (M+ + 1)
7u IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1680 cmminus1 (sharp strong ndashCOndash of acid group) 1650 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 10 (t 6HndashCH3 ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 32 (q 2H ndashCH
2) 120575 34
(q 2H ndashCH2) 70ndash80 (m 9H Ar-H) 106 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 125 154
379 435 1254 1265 1268 1296 1312 1313 1356 13861393 1646 1698 Ms119898119911 = 375 (M+ + 1)
7v IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1687 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 22 (s 1HndashNH) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H
ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m
9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable) 13CNMR(DMSO-d
6 400MHz) 415 459 523 545 1184 1213 1259
1269 1277 1284 1297 1314 1335 1654 1677 Ms119898119911 = 388(M+ + 1)
7w IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash) 1681 cmminus1 (sharp strong ndashCOndash of acid group) 1655 cmminus1
(sharp strong ndashCOndash of amide group) 1H-NMR 120575 12 (t 3HndashCH3) 120575 24 (s 3H ndashCH
3) 120575 26 (q 2H ndashCH
2) 120575 30 (t
2H ndashCH2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndashCH
2) 120575 38
(t 2H ndashCH2) 70ndash80 (m 9H Ar-H) 104 (s 1H ndashNH D2O
exchangeable) 13C NMR (DMSO-d6 400MHz) 124 435
457 473 529 534 1184 1216 1247 1255 1283 1295 13051313 1354 1645 1659 Ms119898119911 = 416 (M+ + 1)
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Advances in
Physical Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom
Analytical Methods in Chemistry
Journal of
Volume 2014
Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
SpectroscopyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
Organic Chemistry International 9
7x IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1690 cmminus1 (sharp strong ndashCOndash of acid group) 1658 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 16 (t3H ndashCH
3) 120575 24 (s 3H ndashCH
3) 120575 30 (t 2H ndashCH
2) 120575 32
(t 2H ndashCH2) 120575 34 (t 2H ndashCH
2) 120575 38 (t 2H ndashCH
2) 70ndash
80 (m 9H Ar-H) 1300 (s 1H ndashNH D2O exchangeable)13C NMR (DMSO-d
6 400MHz) 392 464 473 484 495
1212 1243 1249 1257 1264 1283 1306 1311 1313 16611693 Ms119898119911 = 402 (M+ + 1)
7y IR (KBr) 3100ndash3400 cmminus1 (broad medium ndashNHndash)1675 cmminus1 (sharp strong ndashCOndash of acid group) 1635 cmminus1(sharp strong ndashCOndash of amide group) 1H-NMR 120575 24 (s 3HndashCH3) 120575 30 (t 2H ndashCH
2) 120575 32 (t 2H ndashCH
2) 120575 34 (t 2H ndash
CH2) 120575 38 (t 2H ndashCH
2) 70ndash80 (m 9H Ar-H) 1300 (s 1H
ndashNH D2O exchangeable) 13C NMR (DMSO-d6 400MHz)
489 514 735 745 1196 1214 1225 1238 1247 1257 12641273 1293 1658 1693 Ms119898119911 = 389 (M+ + 1)
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
Acknowledgment
The authors are thankful to the authorities of JawaharlalNehru Technological University Hyderabad for providinglaboratory facilities and for financial support to two of theauthors (Padam Praveen Kumar and Yervala Dathu Reddy)
References
[1] O R Louis and R G Harry ldquoAlcoholysis of alkyl benzyl estersof phthalic acidrdquoThe Journal of Organic Chemistry vol 24 no12 pp 1997ndash2000 1959
[2] P K Dubey S M G Mohiuddin and D Ramesh ldquoReactions ofphthalic anhydride with alcoholsrdquo Asian Journal of Chemistryvol 9 no 3 pp 379ndash387 1997
[3] P A Kober J T Marshall and E N Rosenfeld ldquoPhenolph-thalein and its colorless salts [Third paper] Preparation ofmonobasic phenolphthalatesrdquo Journal of theAmericanChemicalSociety vol 34 no 10 pp 1424ndash1433 1912
[4] D Williamm ldquoSalts of phenolphthaleinrdquo Journal of the Ameri-can Chemical Society vol 54 no 7 pp 2947ndash2951 1932
[5] S A Carlson and D M Hercules ldquoDelayed thermal fluores-cence of anthraquinone in solutionsrdquo Journal of the AmericanChemical Society vol 93 no 22 pp 5611ndash5616 1971
[6] L Lunazzi M Mancinelli and A Mazzani ldquoStereodynamicsand conformational chirality of the atropisomers of ditolylanthrones and anthraquinonerdquo The Journal of Organic Chem-istry vol 73 no 14 pp 5354ndash5359 2008
[7] D Guay G Tourillon L Gastonguay et al ldquoHighly photoactivechemically modified thin films of chloroaluminum (and bro-moaluminum) phthalocyanines probed by NEXAFS and UPSdetermination of the electronic structure and the molecularorientationrdquo Journal of Physical Chemistry vol 95 no 1 pp 251ndash257 1991
[8] P K Dubey S M G Mohiuddin and D Ramesh ldquoAssay ofphthalic anhydride and some related compounds by volumetric
methodsrdquo Asian Journal of Chemistry vol 7 no 3 pp 597ndash6031995
[9] L O Okunrobo C O Usifoh and S O Okpo ldquoReactionsof phthalimides with 1-methylethylamine analgesic and anti-inflammatory properties of resulting carboxamidesrdquo PakistanJournal of Pharmaceutical Sciences vol 19 no 1 pp 34ndash38 2006
[10] V K Pandey and N Raj ldquoSynthesis of 120572-methylarylamido-120573-naphthyl-(1-methylamino-2-methyl-benzimi-dazolyl)-ethersrdquoCurrent Science vol 53 no 5 pp 256ndash258 1984
[11] A M Alaa and A Abdel ldquoNovel and versatile methodologyfor synthesis of cyclic imides and evaluation of their cytotoxicDNA binding apoptotic inducing activities and molecularmodeling studyrdquo European Journal of Medicinal Chemistry vol42 no 5 pp 614ndash626 2007
[12] F L Dunlap and F W Cummer ldquoThe action of the sodiumsalts of dibasic acids on aniline hydrochloride and of anilineon phthalyl chloride and succinyl chloriderdquo Journal of theAmerican Chemical Society vol 25 no 6 pp 612ndash621 1903
[13] A T Dann W Davies A N Hambly R E Paul and G S CSemmens ldquoPhthalyl fluoriderdquo Journal of the Chemical Societypp 15ndash21 1933
[14] E G D de Toranzo and J A Brieux ldquoSyntheses of unsymmetrico-phthalic acid diamidesrdquo Journal of Medicinal Chemistry vol10 no 5 pp 982ndash983 1967
[15] A Reynolds ldquoSynthesis and characterization of some toluidesof o-phthalic acidrdquo The Journal of Organic Chemistry vol 28no 11 pp 3223ndash3225 1963
[16] A El-Faham and F Albericio ldquoPeptide couplingreagents morethan a letter souprdquo Chemical Reviews vol 111 no 11 pp 6557ndash6602 2011
[17] L A Carpino and A El-Faham ldquoTetramethylfluoroformami-dinium hexafluorophosphate a rapid-acting peptide couplingreagent for solution and solid phase peptide synthesisrdquo Journalof the American Chemical Society vol 117 no 19 pp 5401ndash54021995
[18] R Subiros-Funosas G A Acosta A El-Faham and F Alberi-cio ldquoMicrowave irradiation and COMU a potent combinationfor solid-phase peptide synthesisrdquo Tetrahedron Letters vol 50no 45 pp 6200ndash6202 2009
[19] S-Y Han and Y-A Kim ldquoRecent development of peptidecoupling reagents in organic synthesisrdquoTetrahedron vol 60 no11 pp 2447ndash2467 2004
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Advances in
Physical Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom
Analytical Methods in Chemistry
Journal of
Volume 2014
Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
SpectroscopyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
Submit your manuscripts athttpwwwhindawicom
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Inorganic ChemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
International Journal ofPhotoenergy
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Carbohydrate Chemistry
International Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Advances in
Physical Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom
Analytical Methods in Chemistry
Journal of
Volume 2014
Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
SpectroscopyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Medicinal ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Chromatography Research International
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Applied ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Theoretical ChemistryJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Spectroscopy
Analytical ChemistryInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Quantum Chemistry
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Organic Chemistry International
ElectrochemistryInternational Journal of
Hindawi Publishing Corporation httpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
CatalystsJournal of
![4β-[4’-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA ... · 1 4 -[4 -(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA Topoisomerase I and IIα Inhibitors and Apoptosis Inducing](https://static.fdocuments.in/doc/165x107/5e7ee9e4bc140f3b9414d72f/4-4a-1-arylureidobenzamidepodophyllotoxins-as-dna-1-4-4-1-arylureidobenzamidepodophyllotoxins.jpg)
