Sodium Hydroxide → 6-chloro-1-isobutyl-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(6-chloro-1-isobutyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (282.7 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-isobutyl-1H-indole-3-carboxylic acid (161.4 mg, 79%) as a cream-colored solid: mp 205-206° C.; EI-HRMS m/e calcd for C13H14ClNO2 (M+) 251.0713, found 251.0713.

Provenance & Evidence