Chloroacetyl chloride → 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Participants

Reaction Steps

To a solution of (3-quinoxalin-2-ylphenyl)amine (4.43 g, 20 mmol) and Et3N (3 mL, 22 mmol) in THF (100 mL), chloroacetyl chloride (1.6 mL, 20 mmol) was added dropwise with stirring. The solvent was evaporated in vacuo. The residue was slurred with water, filtered, and dried. The solid was dissolved in hot toluene (300 mL), treated with silica gel, filtered and left to recrystallize to afford 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (4.5 g, 76% yield). LCMS calculated for C16H12ClN3O (M+H): 298.75. found 298.06. 1H-NMR (400 MHz, DMSO-d6) δH: 10.6 (1H, br. s), 9.52 (1H, s), 8.54 (1H, m), 8.20-8.05 (3H, m), 7.90-7.70 (3H, m), 7.62-7.51 (1H, m), 4.31 (2H, s).

Provenance & Evidence