Triethylamine → N-{4-[(3-Chlorophenyl)amino]-3-cyano-6-quinolinyl}-2-propenamide

Participants

Reaction Conditions

Reaction Steps

Dissolved 430 mg (1.46 mmol) 6-amino-4-[(3-chlorophenyl)amino]-3-quinolinecarbonitrile in 4 ml DMF, added 10 ml THF and chilled to 0° C. under N2. Added 224 μl (1.60 mmol) triethylamine and 133 μl (1.60 mmol) acryloyl chloride. Removed ice bath at 15 minutes, reaction complete at this time, but stirred overnight at 25° C. Stripped solvent, added a dilute sodium bicarbonate to the residue and collected solids. Washed with water and dried in vacuo. Boiled in ethyl acetate, collected solids and dried in vacuo, giving 200 mg of orange solid: mass spectrum (electrospray m/e): M+H=349.0, 351.0.

Provenance & Evidence