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

Participants

Reaction Conditions

Reaction Steps

A 500 mL, three-necked flask equipped with a thermocouple, condenser, and addition funnel was charged with indole-3-acetonitrile (10.0 g, 0.064 mol), potassium carbonate (5.0 g, 36 mmol), N,N-dimethylformamide (60 mL) and dimethyl carbonate (11.0 mL, 0.13 mol). The resulting mixture was heated to 124±1° C. The progress of the reaction was monitored by HPLC. After 10 h at this temperature, the presence of the starting indole could not be detected. The reaction mixture was then cooled to zero to −5° C. Water (140 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 (I and II, 9.69 g, 89%) as a brown solid.

Provenance & Evidence