Sodium Cyanide → HCID 22048415, compound

Participants

Reaction Steps

To a stirred solution of 1-(3-sec-butoxy-benzyl)-4-chloromethyl-6,7-dimethoxy-isoquinoline (950 mg, 2.38 mmol) in methyl sulfoxide (10 mL) was added sodium cyanide (582, 11.9 mmol). The reaction mixture was stirred at room temperature for 1 h and diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (3×25 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 40% ethyl acetate/hexane) afforded [1-(3-sec-butoxy-benzyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetonitrile (850 mg, 91% yield) as a colorless oil.

Provenance & Evidence