Hydrochloric Acid → 6-Hydroxy-1H-indole-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

146 ml (146 mmol) of 1M boron tribromide in methylene chloride are added slowly, at 0° C., to a solution of 10 g (48.73 mmol) of methyl 6-methoxy-2-indole carboxylate in 500 ml of methylene chloride. The reaction medium is stirred at 0° C. for 1 h and at ambient temperature for 2 h. The reaction medium is cooled to 0° C. and 100 ml (100 mmol) of 1M boron tribromide in methylene chloride are added slowly, at 0° C. The reaction is stirred at 0° C. for 1 h and at ambient temperature for 16 h. The reaction medium is then cooled to approximately 0° C. and a 1N hydrochloric acid solution (247 ml) is added slowly with stirring. The mixture obtained is filtered over sintered glass. The organic phase (methylene chloride) of the filtrate is separated and the aqueous phase is then acidified with 5N hydrochloric acid and extracted with ethyl acetate. The organic phase (ethyl acetate) is dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure, to give 6.39 g of 6-hydroxy-1H-indole-2-carboxylic acid in the form of a brown solid.

Provenance & Evidence