Acetic Acid → 3-Methyl-9h-pyrido[3,4-b]indole

Participants

Reaction Conditions

Reaction Steps

2 g of 3-hydroxymethyl-β-carboline, 3.7 g of sodium iodide and 2.5 ml of chlorotrimethylsilane are stirred in 50 ml of N,N-dimethylformamide at a bath temperature of 35° C. for 4 hours. 3 g of zinc powder and 10 ml of glacial acetic acid are added to the resulting yellow suspension and stirred for another 18 hours at 80° C. The reaction mixture is allowed to clarify on Celite and the filtrate is concentrated under vacuum. The resulting oil is chromatographed on silica gel (methylene chloride/ethanol: 9+1). 0.825 g of 3-methyl-β-carboline with a 255°-256° C. melting point was obtained.

Provenance & Evidence