Potassium Hydroxide → 5-Bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic Acid

Participants

Reaction Steps

To a stirred solution of 5-bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic acid ethyl ester (2.3 g, 5.7 mmol) in ethanol/water (2:1, 45 ml) at room temperature was added potassium hydroxide (0.96 g, 17.1 mmol). The solution was warmed to reflux for about 3 hours, cooled, and most of the ethanol was removed under reduced pressure. To the residue was added water, 0.5N sodium hydroxide and methylene chloride, and the two-phase mixture was suction filtered to remove some insoluble material. The aqueous layer was acidified to pH 2 with 6N hydrochloric acid, and the precipitate was filtered off, washed with water, and air dried to afford the title compound, (1.66 g).

Provenance & Evidence