1,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile → 2-Chloro-6-methyl-5-phenylnicotinonitrile

Participants

Reaction Steps

A mixture of 100.34 g 3-cyano-6-methyl-5-phenyl-1H-pyridin-2-one [Walker and Weaver, J. Org. Chem. 26, 4441 (1961)]and 192 ml phenylphosphonic dichloride (C6H5POCl2) was warmed to 160-170° C. and kept at that temperature for about 16 hours. The reaction mixture was cooled and poured into ice water. The solid product was collected, dried in a vacuum oven and extracted with ether. The ether solution was concentrated, and the residue was washed with hexane and extracted with 300 ml 15% aqueous potassium bicarbonate. The resulting solid was dried in a vacuum oven to give 92.71 g (85%) 2-chloro-3-cyano-6-methyl-5-phenylpyridine, m.p. 134-135° C.

Provenance & Evidence