Dimethyl Sulfoxide → 1-(4-Chlorophenyl)isoquinoline-5-acetonitrile

Participants

Reaction Steps

To a mixture of 5.0 g of sodium cyanide and 120 ml of dimethylsulfoxide was added 11.7 g of 1-(4-chlorophenyl)-5-chloromethylisoquinoline little by little. The mixture was stirred at room temperature for 2 hours, and poured into a mixture of ethyl acetate and 1% sodium bicarbonate aqueous solution. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried. The solvent was distilled off. Recrystallization of the residue from dichloromethane-hexane afforded 1-(4-chlorophenyl)isoquinoline-5-acetonitrile as slightly yellow prisms having a melting point of 131.5° to 132.5° C.

Provenance & Evidence