Dimethylformamide → 5-Chloro-1-methylindole

Participants

Reaction Conditions

Reaction Steps

6-Chloroindole (1.0 g, 6.59 mmol), potassium carbonate (0.5 g), N,N-dimethylformamide (10 mL) and dimethyl carbonate (1.7 mL, 20.21 mmol) were stirred and heated to reflux (˜130° C.). The starting indole was consumed within 3.5 h (as determined by HPLC). After the mixture was then cooled to ˜3° C., ice cold water (50 mL) was added and the resulting oily suspension was extracted with tert-butyl methyl ether (40 mL). The separated organic layer was washed with water (3×25 mL), then was evaporated under vacuum to furnish 5-chloro-1-methylindole as a light yellow oil (1.05 g, 96.1% yield).

Provenance & Evidence