Quinoline → 1-Benzoyl-1,2-dihydroquinaldonitrile

Participants

Reaction Steps

A mixture of quinoline (19.35 g), benzoyl chloride (28.1 g), aluminum chloride (1.0 g) and methylene chloride (500 mL) was stirred at ambient temperature for 10 minutes. Trimethyl silyl cyanide (20.0 g) was added dropwise. The stirring was continued for 4 hours. The mixture was washed twice with 1N HCl (500 mL) then with water (500 mL). The organic phase was dried over anhydrous magnesium sulfate then evaporated to dryness. The title compound (26.0 g) was obtained as a white solid, m.p. 153-154° C. This product was used for the preparation of the title compound described in step 2, and for preparation of the title compound described in Example 2.

Provenance & Evidence