Hydrochloric Acid → 5-(Trifluoromethyl)-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.01 g of methyl 5-(trifluoromethyl)-1H-indole-3-carboxylate in 12 mL of MeOH and 12 mL of THF, 6 mL of 1 M aqueous sodium hydroxide solution was added, and the resulting mixture was stirred at 80° C. overnight. To the solution, 3 mL of 1 M aqueous sodium hydroxide solution was further added, and the resulting mixture was stirred at 80° C. for 6 hours. To the solution, 9 mL of 1 M hydrochloric acid and 60 mL of water were added, the precipitated solid was collected by filtration, and the solid obtained was purified by silica gel column chromatography (chloroform-methanol=100:1 →150:1→20:1) and then washed with hexane to obtain 0.71 g of 5-(trifluoromethyl)-1H-indole-3-carboxylic acid as a cream-colored solid. FAB−: 228

Provenance & Evidence