Reaction #6909

Reaction equation

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

sodium cyanide

→

title compound

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

Conditions

Workup

1. 1
   Otherequipped with a reflux condenser
2. 2
   Otherpurge cycles
3. 3
   workup.ADDITIONfollowed by the addition of acetonitrile (25 mL)
4. 4
   TemperatureThe reaction was heated
5. 5
   Temperatureto reflux for 5 hours
6. 6
   TemperatureAfter cooling
7. 7
   workup.ADDITIONthe reaction was diluted with ethyl acetate (200 mL)
8. 8
   Filtrationfiltered through CELITE diatomaceous earth
9. 9
   Washrinsed with copious amounts of ethyl acetate
10. 10
    WashThe organic solution was washed twice with brine (50 mL)
11. 11
    Dryingdried over sodium sulfate
12. 12
    Filtrationfiltered through a fritted funnel
13. 13
    Otherthe volatiles were removed under vacuum
14. 14
    OtherThe crude residue was crystallized from methanol, which

Procedure

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.

Source