Potassium Carbonate → 1-Methyl-1H-indole-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of indole-3-carbonitrile (1.0 g, 7.03 mmole), potassium carbonate (0.5 g), N,N-dimethytformamide (10 mL) and dimethyl carbonate (1.8 mL, 21.4 mmol) was stirred and heated to reflux (˜130° C.). The reaction (monitored by HPLC) was complete within 3.5 h. The reaction mixture was then cooled to 3° C. and ice cold water (25 mL) was added slowly. The resulting oily suspension was extracted with tert-butyl methyl ether (40 mL) and the organic phase was washed with water (3×25 mL), dried and evaporated in vacuo to obtain 1.07 g of the product, 1-methylindole-3-carbonitrile, as a dark oil (97.4% yield).

Provenance & Evidence