Methyl iodide → 4-Chloro-1-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

A mixture of 60 g of 4-chloro-1H-indole, 400 ml of benzene, 200 ml of a 50% solution of sodium hydroxide, 68 g of n-tetrabutylammonium acid sulfate and 68 ml of methyl iodide was heated at 40° C. with agitation for 4 hours and was then cooled and decanted. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried and distilled to dryness under reduced pressure. The residue was purified by chromatography on silica gel and elution with an 8-2 mixture of cyclohexane and benzene to obtain 63.85 g of 4-chloro-1-methyl 1H-indole.

Provenance & Evidence