Potassium Hydroxide → (5-fluoro-2-methyl-1H-indol-3-yl)acetic acid

Reaction equation

C([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][C:7]=1[CH3:16])C.[OH-].[K+]>CO.O>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:16])=[C:6]2[CH2:5][C:4]([OH:17])=[O:3]

Participants

Procedure

This ester (4.5 g, 0.019 mol.) was added to a solution of KOH (2.13 g, 38 mmol.) in methanol (100 ml), and the mixture was heated at reflux for 30 min. For working up, the mixture was diluted with water (100 ml) and methanol was distilled off using a rotary evaporator. The aqueous phase was adjusted to pH 4 with 2M HCl and stored for 2 h at 4° C. The white solid that precipitated was filtered off with suction and washed with methanol. (5-Fluoro-2-methyl-1H-indol-3-yl)acetic acid was obtained in a yield of 3.25 g (m.p. 136–138° C.).