N-methyl-2-pyrrolidone → HCID 20242569, compound

Participants

Reaction Steps

A solution of 1-(4-bromophenyl)-1,4-dihydroisoquinol-3-one (15.1 g, 50 mmol) and cuprous cyanide (8.95 g, 100 mmol) in N-methylpyrrolidinone (150 ml) was heated under reflux under a nitrogen atmosphere for 2 h. The solution was cooled and diluted with 10% aqueous ethylenediamine solution (1000 ml), then extracted with ethyl acetate (4×250 ml). The combined extracts were washed with water (4×250 ml) and brine (250 ml), then dried (MgSO4) and evaporated to dryness to leave a pale brown solid which was crystallised from ethyl acetate to give the title compound (8.43 g, 68%), m.p. 165°-168° C. (ethanol).

Provenance & Evidence