Hydrochloric Acid → 4-(2-oxo-2,3-dihydro-1H-indol-3-yl)butanoic acid

반응식

Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.CS(C)=[O:19]>O>[O:19]=[C:3]1[CH:4]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2]1

참가 물질

실험 절차

Concentrated HCl (16.6 mL) was added dropwise with stirring, over 10 minutes, to a solution of 4-(3-indolyl)butanoic acid [II: R1 =R3 =H, R2 =(CH2)3COOH] (2.00 g) in DMSO (7.0 mL) at room temperature (method of Savige WE, Fontana A, J. Chem. Soc. Chem. Commun. 1976:599). After 15 minutes reaction, the mixture was diluted with water (80 mL) and extracted with EtOAc (4×100 mL). Removal of the solvent gave crude 4-(2-oxo-3-indolinyl)butanoic acid [III: R1 =R3 =H, R2 =(CH2)3COOH] (2.07 g, 96%) as a green-brown solid; mp (water) 169°-171° C. (Hinman RL, Bauman CP, J. Org. Chem, 1964;29:1206 record mp 170°-171° C.).