Sodium Hydroxide → HCID 59425917, compound

Participants

Reaction Steps

A solution of methyl 3-cyano-1-ethyl-1H-indole-6-carboxylate (1.60 g, 7.02 mmol), prepared by the method described in example 1A from methyl 1H-indole-6-carboxylate, in THF (35 mL) was treated with 1N NaOH (7.7 mL, 7.7 mmol) and heated at reflux for 2.5 h. After cooling to room temperature, most of the THF was removed and the solution was diluted with H2O and extracted with ether (2×). The ether extracts were discarded. The aqueous phase was then acidified with 6N HCl to pH 2 and then extracted with EtOAc (3×). The EtOAc layers were combined, washed with saturated NaCl and then dried and concentrated to afford 1.43 g (95%) of 3-cyano-1-ethyl-1H-indole-6-carboxylic acid as a white solid.

Provenance & Evidence