3-(1-OXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)PROPANOIC ACID synthesis
- Product Name:3-(1-OXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)PROPANOIC ACID
- CAS Number:83747-30-2
- Molecular formula:C11H11NO3
- Molecular Weight:205.21
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887643-32-5
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83747-30-2
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Yield:83747-30-2 90%
Reaction Conditions:
with zinc perchlorate in water at 20; for 2.25 h;
Steps:
Synthesis of 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid
The ligand, Hpda was prepared following our published procedure[28]. To a solution of the precursor ligand H2cbal (0.500 g,2.242 mmol) in 15 ml of water at room temperature was slowlyadded Zn(ClO4)26H2O (0.417 g, 1.119 mmol) dissolved in 10 mlof water for a period of 15 min. After complete addition, a colorlessclear solution was observed. The whole reaction mixture was stirredfor 2 h at room temperature. The solvent was then rotary evaporated.The off-white precipitate isolated was washed withmethanol followed by diethyl ether and hexane. The product wasrecrystallized from a concentrated water solution of the compound.The product was then dried in vacuo over anhydrous calciumsulfate. Yield: 0.207 g (90%). Anal. Calcd. for C11H11NO3: C,64.38%; H, 5.40%; N, 6.82%. Found: C, 64.14%; H, 5.57%; N, 6.64%.FTIR (KBr pellet, cm1): m = 1695(s), 1595(s), 1371(s), 1339(s),1220(s), 1173(s), 934(s), 826(s), 761(s). 1H NMR (400 MHz, D2O,25 C): d 2.79 (t, 2H, ethylenic), 3.89 (t, 2H, ethylenic), 4.54 (s,2H, methylenic protons of the isoindol ring), 7.51-7.73 (m, 4H, aromatic).13C NMR (400 MHz, D2O, 25 C): d 35.31 (1C, CH2), 42.88(1C, CH2), 49.17 (1C, CH2 of the iosindol ring), 126.50 (1C, aromaticCH), 127.00 (1C, aromatic CH), 127.91 (1C, aromatic CH), 129.34(1C, aromatic CH), 134.10 (1C, aromatic CH), 135.72 (1C, aromaticCH), 171.56 (1C, CO of the isoindol ring), 177.21 (1C, aliphatic carboxylic).
References:
Patra, Ayan;Sen, Tamal K.;Musie, Ghezai T.;Mandal, Swadhin K.;Bera, Manindranath [Journal of Molecular Structure,2013,vol. 1047,p. 317 - 323]
3339-73-9
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4561-06-2
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83747-30-2
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