3-Quinolinecarboxaldehyde → HCID 46841409, compound

Participants

Reaction Steps

3-Quinoline carboxaldehyde (0.41 mmol) and anhydrous CuCl2 (0.110 g, 0.82 mmol) were added to a solution of 2-amino-N-(4-chlorophenyl)benzamide (0.100 g, 0.41 mmol) in anhydrous EtOH (10 mL). The mixture was heated at reflux temperature for 4 hours and concentrated in vacuo. The residue was dissolved in EtOAc and washed with H2O and brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography on silica gel, eluting with 5% to 50% EtOAc in heptane, afforded the title compound as a white solid (14%). 1H-NMR (300 MHz, DMSO-d6): δ 8.83 (d, J=2.1 Hz, 1H), 8.45 (d, J=1.8 Hz, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.88-8.03 (m, 3H), 7.74-7.88 (m, 2H), 7.56-7.73 (m, 2H), 7.52 (d, J=8.6 Hz, 2H), 7.40 (d, J=8.7 Hz, 2H). MS (APCI) m/z: 384 (M+H)+.

Provenance & Evidence