6-Iodoquinazolin-4-one → 4-Hydroxyquinazoline-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

6-Iodoquinazolin-4-one (10 g) in 1-methyl-2-pyrrolidinone (50 ml) was treated with copper (I) cyanide (4.28 g) at 206° C. under N2 for 16 hours. The resulting mixture was cooled to 170° C. and the methyl-2-pyrrolidinone removed by vacuum distillation. Potassium cyanide (2.4 g) in water (30 ml) and ethyl acetate (150 ml) were added to the cooled residue and heating continued at 110° C. for 1.5 hours. This mixture was then filtered hot through a pad of celite and the filter cake washed thoroughly with ethyl acetate. Subsequent separation, drying and concentration in vacuo gave the title compound (2.29 g) as a beige solid; δH [2H6]DMSO 12.65(1H, bs), 8.53(1H, d), 8.28(1H, s), 8.19(1H, dd), 7.82(1H, d); m/z (M−1+) 171.

Provenance & Evidence