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

Participants

Reaction Steps

To a mixture of 2.5 g of sodium cyanide and 150 ml of dimethylsulfoxide was added 14 g of 1-(4-bromophenyl)-5-chloromethylisoquinoline little by little. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a mixture of ethyl acetate and a dilute aqueous solution of sodium bicarbonate. The organic layer was separated, dried, and recrystallized from dichloromethane-hexane to afford 8.5 g of 1-(4-bromophenyl)isoquinoline-5-acetonitrile as colorless prisms having a melting point of 121.5° to 122.5° C.

Provenance & Evidence