Sodium Hydroxide → HCID 22497233, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[6-chloro-1-(3-methyl-butyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone (284.9 mg, 0.81 mmol) in a 20% aqueous sodium hydroxide solution (2.7 mL) was heated under reflux for 17 h. At this time, the reaction was cooled to 25° C. and was diluted with water (75 mL). This mixture was extracted with diethyl ether (1×50 mL). The aqueous layer was acidified to pH=1 with concentrated hydrochloric acid and then extracted with ethyl acetate (1×75 mL). The combined organic layers were washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 6-chloro-1-(3-methyl-butyl)-1H-indole-3-carboxylic acid (149.3 mg, 69.5%) as a light orange solid: mp 53-55° C.; EI-HRMS m/e calcd for C14H16ClNO2 (M+) 265.0870, found 265.0860.

Provenance & Evidence