Reaktion #6909

Reaktionsgleichung

6-Iodo-3,4-dihydroquinolin-2(1H)-one

sodium cyanide

→

title compound

2-Oxo-1,2,3,4-tetrahydroquinoline-6-carbonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a reflux condenser
2. 2
   Sonstigepurge cycles
3. 3
   workup.ADDITIONfollowed by the addition of acetonitrile (25 mL)
4. 4
   TemperaturThe reaction was heated
5. 5
   Temperaturto reflux for 5 hours
6. 6
   TemperaturAfter cooling
7. 7
   workup.ADDITIONthe reaction was diluted with ethyl acetate (200 mL)
8. 8
   Filtrationfiltered through CELITE diatomaceous earth
9. 9
   Waschenrinsed with copious amounts of ethyl acetate
10. 10
    WaschenThe organic solution was washed twice with brine (50 mL)
11. 11
    Trocknendried over sodium sulfate
12. 12
    Filtrationfiltered through a fritted funnel
13. 13
    Sonstigethe volatiles were removed under vacuum
14. 14
    SonstigeThe crude residue was crystallized from methanol, which

Vorschrift

6-Iodo-3,4-dihydroquinolin-2(1H)-one (1.50 g; 5.50 mmol), sodium cyanide (0.54 g; 11.0 mmol), copper (I) iodide (0.105 g; 0.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.32 g; 0.3 mmol) were combined in a flask equipped with a reflux condenser. The flask was subjected to several evacuation-nitrogen purge cycles followed by the addition of acetonitrile (25 mL). The reaction was heated to reflux for 5 hours. After cooling, the reaction was diluted with ethyl acetate (200 mL), filtered through CELITE diatomaceous earth and rinsed with copious amounts of ethyl acetate. The organic solution was washed twice with brine (50 mL), dried over sodium sulfate, filtered through a fritted funnel, and the volatiles were removed under vacuum. The crude residue was crystallized from methanol, which afforded the title compound.

Quelle