反应详情

To a solution of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (276 mg, 0.93 mmol) in EtOH (8 mL), NaCN (50 mg, 1.02 mmol) was added and the reaction mixture was heated at reflux for 21 hrs. After cooling to room temperature, water (10 mL) was added and the reaction mixture was extracted with ethyl acetate (20 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, and the residue was purified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane, then ethyl acetate up to 50% over 20 min). The isolated solid was triturated with Et2O (10 mL) and filtered to afford 2-cyano-N-[3-(quinoxalin-2-yl)phenyl]acetamide as a light-yellow solid (27 mg, 10% yield). LCMS calculated for C17H12N4O (M+H): 289.30. found 289.00. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.55 (1H, br. S), 9.52 (1H, s), 8.48 (1H, m), 8.20-8.12 (2H, m), 8.10 (1H, d, J=7 Hz), 7.98-7.80 (3H, m), 7.58 (1H, m), 3.95 (2H, s).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 21 hrs
3. extractionthe reaction mixture was extracted with ethyl acetate (20 mL)
4. washThe organic phase was washed with brine (20 mL)
5. dry with materialdried over MgSO4
6. customthe residue was purified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane
7. customThe isolated solid was triturated with Et2O (10 mL)
8. filtrationfiltered