Reaktion #2133100

Reaktionsgleichung

water

2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

NaCN

→

2-cyano-N-[3-(quinoxalin-2-yl)phenyl]acetamide

Ausbeute 10.1%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturat reflux for 21 hrs
3. 3
   Extraktionthe reaction mixture was extracted with ethyl acetate (20 mL)
4. 4
   WaschenThe organic phase was washed with brine (20 mL)
5. 5
   Trocknendried over MgSO4
6. 6
   Sonstigethe residue was purified by flash chromatography (Flash Master, 5 g Isolute Silica column, gradient 0 to 5 min hexane
7. 7
   SonstigeThe isolated solid was triturated with Et2O (10 mL)
8. 8
   Filtrationfiltered

Vorschrift

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).

Quelle