Thionyl Chloride → 2-Chloro-6-methoxyquinoline-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (7.9 ml) was added dropwise over a 12 min period to a stirred solution of 16.3 g 2-chloro-6-methoxy-3-quinolinecarboxaldehyde oxime in 160 ml dimethylformamide at 0° C. The reaction mixture was stirred for 15 min longer at 0° C. and then at room temperature overnight. The mixture was then quenched in ice-water, and the yellow solid product was collected, washed with water and dried in vacuo at 75° C. to give 14.8 g 2-chloro-6-methoxy-3-quinolinecarbonitrile, m.p. 201°-202° C.

Provenance & Evidence