반응 #6909

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

sodium cyanide

→

title compound

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

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후처리

1. 1
   기타equipped with a reflux condenser
2. 2
   기타purge cycles
3. 3
   workup.ADDITIONfollowed by the addition of acetonitrile (25 mL)
4. 4
   온도The reaction was heated
5. 5
   온도to reflux for 5 hours
6. 6
   온도After cooling
7. 7
   workup.ADDITIONthe reaction was diluted with ethyl acetate (200 mL)
8. 8
   여과filtered through CELITE diatomaceous earth
9. 9
   세척rinsed with copious amounts of ethyl acetate
10. 10
    세척The organic solution was washed twice with brine (50 mL)
11. 11
    건조dried over sodium sulfate
12. 12
    여과filtered through a fritted funnel
13. 13
    기타the volatiles were removed under vacuum
14. 14
    기타The crude residue was crystallized from methanol, which

실험 절차

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.

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