Potassium Hydroxide → HCID 18344915, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-5-ethoxycarbonylmethyl-2-methyl-1H-indole-3-carboxylic acid ethyl ester (3 g, 8.1 mmol) in ethanol (30 mL) is added 4.6N KOH (3 mL; 9.8 mmol), and the reaction mixture is stirred at 45° C. for 4 hours and then at room temperature overnight. The solution is concentrated in vacuo and then ethyl acetate (150 mL) and water (150 mL) are added. The organic layer is extracted with water (50 mL), the combined water layers are then acidified with HCl (20%) to pH<2. The aqueous layers are then extracted with ethyl acetate (2×100 mL), dried (Na2SO4), filtered, and concentrated to give the desired product (1.85 g, 66%). MS: 340, 342 (M+1)+.

Provenance & Evidence