反应详情

A suspension of methyl quinoxaline-6-carboxylate (2.00 g) in methanol (7.0 mL) and 28-30% ammonia (14 mL) was stirred in a sealed tube at room temperature for 16 h. The precipitated solid was filtered, washed with water and dried under high vacuum to give quinoxaline-6-carboxamide as a white powder. A portion of this material (0.10 g) was suspended in anhydrous dichloromethane and treated with oxalyl chloride (1.0 mL of a 2M solution in dichloromethane) under a nitrogen atmosphere. The mixture was heated at reflux for 16 h and concentrated under reduced pressure. The residue was dissolved in anhydrous tetrahydrofuran (1 mL) and added to an ice-cooled solution of 3-aminobiphenyl (0.98 g) in anhydrous tetrahydrofuran (1 mL). The mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue taken up in methanol and filtered to give N-{[(3-phenylphenyl)-amino]carbonyl}quinoxalin-6-ylcarboxamide as a white powder. 1H NMR (DMSO-d6) δ 7.37-7.47 (m, 3H), 7.50 (t, J=7.2 Hz, 2H), 7.65 (d, J=7.8 Hz, 1H), 7.69 (d, J=7.2 Hz, 2H) 7.91 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 8.37 (dd, J=8.8, 1.9 Hz, 1H), 8.84 (d, J=1.9 Hz, 1H), 9.09 (s, 2H), 10.85 (s, 1H), 11.44 (s, 1H). MS (ES) m/z 369.

1. filtrationThe precipitated solid was filtered
2. washwashed with water
3. customdried under high vacuum