Acetic Anhydride → N-(3,4-Dichlorobenzyl)-5-acetoxyindole-2-carboxylic acid

反応式

[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([OH:18])=[O:17].[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:23](=[O:25])[CH3:24])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([OH:18])=[O:17]

参加物

実験手順

To a solution of N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acid (10 g) in warm ethyl acetate (250 ml) was added 4-dimethylaminopyridine (100 mg) and acetic anhydride (5.0 ml) and the resulting mixture was stirred for 2 hours. The organics were washed with 1N HCl and dried. Hexane was added to cause crystallision of the product. The solid was filtered and washed with hexane to give the desired product. (5 g, 44%). 1H NMR (DMSO-d6) δ 2.25 (s, 3H), 5.85 (s, 2H), 6.9 (dd, 1H), 7.05 (dd, 1H), 7.3-7.6 (m, 5H); m/z 378, 380 (MH+).