Hydrochloric Acid → 6-chloro-5-(2-fluoro-4-methoxyphenyl)-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-chloro-5-(2-fluoro-4-methoxyphenyl)-1H-indole-3-carboxylate (50 mg, 0.15 mmol) in methanol (1.5 mL) and aqueous 1M sodium hydroxide (1M, 0.50 mmol, 0.50 mL) was heated at 75° C. for 24 hours. The reaction was then acidified with 1M HCl to pH=2 and diluted with ethyl acetate. The layers were separated and the aqueous layer was back-extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a crude solid. A small amount of methylene chloride was added and the crude material slurried for 5 minutes. The solid was then filtered and washed with ethyl acetate to provide the title compound (13 mg, 27% yield).

Provenance & Evidence