Indole → 2-(1-methyl-1H-indol-3-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

A 1 L, three-necked flask equipped with a thermocouple, condenser, and addition funnel was charged with indole-3-acetonitrile (58.0 g, 90% pure=0.334 mol), tetrabutylammonium bromide (11.6 g, 36 mmol), N,N-dimethylformamide (348 mL) and dimethyl carbonate (92.8 mL, 1.10 mol) and the resulting mixture was heated to 126±1° C. The progress of the reaction was monitored by HPLC and after 3 h at this temperature, the presence of remaining starting indole could not be detected. After the reaction mixture was then cooled to zero to −5° C., water (696 mL) was added which resulted in the formation of a precipitate. The mixture was stirred at −5° C. for 1 hour, then the solid was collected by filtration, washed with water (150 mL) and dried under high vacuum at 45° C. for 24 h to give 1-methylindole-3-acetonitrile (52.0 g, 91.5%) as a brown solid.

Provenance & Evidence