1-benzoyl-2H-quinoline-2-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(Benzoyl)-1,2-dihydro-quinoline-2-carbonitrile (26.0 g) was dissolved in acetone (500 mL). Solid sodium bicarbonate (15 g) was added. The mixture was stirred for 30 minutes. 30% Hydrogen peroxide solution (250 mL of a 30% solution) was added drop-wise. After stirring for 4 hours, the acetone was evaporated under vacuum. The residue was acidified with 1N HCl. The precipitate was collected, washed with water and air dried. The solid was slurried in ether then filtered. The title compound (15.3 g) was obtained as an off-white solid, m.p. 169-171° C. After stirring for 4 hours the acetone was evaporated under vacuum The precipitate was collected washed with water and air dried then filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The stirring was continued for 4 hours The mixture was washed twice with 1N HCl (500 mL) The organic phase was dried over anhydrous magnesium sulfate then evaporated to dryness