Реакция #6909

Уравнение реакции

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

sodium cyanide

→

title compound

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

Условия реакции

Обработка

1. 1
   Другоеequipped with a reflux condenser
2. 2
   Другоеpurge cycles
3. 3
   workup.ADDITIONfollowed by the addition of acetonitrile (25 mL)
4. 4
   ТемператураThe reaction was heated
5. 5
   Температураto reflux for 5 hours
6. 6
   ТемператураAfter cooling
7. 7
   workup.ADDITIONthe reaction was diluted with ethyl acetate (200 mL)
8. 8
   Фильтрацияfiltered through CELITE diatomaceous earth
9. 9
   Промывкаrinsed with copious amounts of ethyl acetate
10. 10
    ПромывкаThe organic solution was washed twice with brine (50 mL)
11. 11
    Сушкаdried over sodium sulfate
12. 12
    Фильтрацияfiltered through a fritted funnel
13. 13
    Другоеthe volatiles were removed under vacuum
14. 14
    ДругоеThe crude residue was crystallized from methanol, which

Методика

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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