Reacción #6909

Ecuación de reacción

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

sodium cyanide

→

title compound

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

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a reflux condenser
2. 2
   Otropurge cycles
3. 3
   workup.ADDITIONfollowed by the addition of acetonitrile (25 mL)
4. 4
   TemperaturaThe reaction was heated
5. 5
   Temperaturato reflux for 5 hours
6. 6
   TemperaturaAfter cooling
7. 7
   workup.ADDITIONthe reaction was diluted with ethyl acetate (200 mL)
8. 8
   Filtraciónfiltered through CELITE diatomaceous earth
9. 9
   Lavadorinsed with copious amounts of ethyl acetate
10. 10
    LavadoThe organic solution was washed twice with brine (50 mL)
11. 11
    Secadodried over sodium sulfate
12. 12
    Filtraciónfiltered through a fritted funnel
13. 13
    Otrothe volatiles were removed under vacuum
14. 14
    OtroThe crude residue was crystallized from methanol, which

Procedimiento

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.

Fuente