Benzoyl chloride → 1-Benzoyl-6-chloro-1,2-dihydroquinoline-2-carbonitrile

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Reaction Steps

A solution of 6-chloroquinoline (9.5 g), benzoyl chloride (13.2 g) in methylene chloride (50 mL) was treated with AlCl3 (0.10 g) followed by dropwise addition of trimethyl silyl cyanide (12.5 mL). After 0.5 hour, the mixture was diluted with 150 mL of methylene chloride and washed with water, 1N HCl, saturated sodium bicarbonate (aq.), and brine. The organic phase was dried over magnesium sulfate then evaporated to dryness. The residue was purified by column chromatography on silica gel using ethyl acetate/hexane (3:7) as the eluting solvent. The title compound (13 g) was obtained as a white solid, m.p. 141-143° C. This product was used for the preparation of the title compound described in step 2.

Provenance & Evidence