Benzoyl chloride → N-benzoyl-5-methylindole

Participants

Reaction Steps

To a solution of 5-methylindole (1.0 g, 7.6 mmol) in 8.0 mL of CH2Cl2 was added N,N-dimethylamino pyridine (0.186 g, 1.52 mmol), 2.12 mL (15.24 mmol) of triethylamine and 0.97 mL (1.18 g, 8.39 mmol) of benzoyl chloride. The resulting solution was stirred for 16 hours at room temperature. The solution was diluted with 500 mL of CH2Cl2 and washed with 200 mL of saturated aqueous NaHCO3 and 200 mL of brine. The organic phase was dried over MgSO4, filtered, and concentrated to a yellow oil. The resultant oil was flash chromatographed eluting with 20% ethyl acetate in hexane yielding 1.73 g (96%) of the titled compound as a white powder.

Provenance & Evidence