N-Phenylanthranilic Acid → 3-Hydroxy-1-(4-methoxyphenyl)-1H-indole-2-carboxylic acid methyl ester

반응식

[CH3:1][O:2][C:3]([C:5]1[N:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[CH3:21][O:22]C1C=CC(NC2C=CC=CC=2C(O)=O)=CC=1.C1(NC2C=CC=CC=2C(O)=O)C=CC=CC=1>>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:15]2[CH:20]=[CH:19][C:18]([O:22][CH3:21])=[CH:17][CH:16]=2)[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4]

참가 물질

반응물 3

HCID 4386N-Phenylanthranilic Acid

HCID 2029182-[(4-Methoxyphenyl)amino]benzoic acid

HCID 54687160Methyl 3-hydroxy-1-phenyl-1H-indole-2-carboxylate

생성물 1

HCID 547384473-Hydroxy-1-(4-methoxyphenyl)-1H-indole-2-carboxylic acid methyl ester

실험 절차

Prepared in a manner analogous to the multi-step procedure described [P. Friedlander and K. Kunz, Chem. Ber., 55, 1597 (1922)] for the preparation of 3-hydroxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester, with 2-(4-methoxyphenylamino)benzoic acid substituted for 2-(phenylamino)benzoic acid in the first step of the synthetic sequence. The final indole product was recrystallized from 2-propanol to yield analytically pure product, mp 153°-155° C.