6-Methyl-3-pyridinecarboxaldehyde → HCID 46842157, compound

Participants

Reaction Steps

2-amino-N-(4-cyclopropylphenyl)benzamide (0.342 g, 1.36 mmol), 6-methylnicotinaldehyde (0.197 g, 1.63 mmol), and anyhydrous CuCl2 (0.547 g, 4.08 mmol) were combined in anyhydrous EtOH (30 mL) and heated at reflux for 2.5 hours. After concentration, ethyl acetate (200 mL) was added, and the mixture was washed with water (2×100 mL), dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel, eluting with 20% ethyl acetate/hexanes to 30% ethyl acetate/hexanes to 100% ethyl acetate, plus further purification by flash chromatography on silica gel, eluting with 1:1 ethyl acetate/CH2Cl2, afford the title compound as a white solid (0.070 g, 15%). 1H-NMR (300 MHz, DMSO-6): δ8.44 (d, J=2.0 Hz, 1H), 8.18-8.20 (m, 1H), 7.88-7.94 (m, 1H), 7.77 (d, J=7.6 Hz, 1H), 7.58-7.65 (m, 2H), 7.22 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.1 Hz, 1H), 7.04 (d, J=8.4 Hz, 2H), 2.40 (s, 3H), 1.84-1.91 (m, 1H), 0.91-0.99 (m, 2H), 0.63-0.68 (m, 2H). MS (APCI) m/z: 354 (M+H)+.

Provenance & Evidence