反応 #6909

反応方程式

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

sodium cyanide

→

title compound

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

反応条件

後処理

1. 1
   その他equipped with a reflux condenser
2. 2
   その他purge cycles
3. 3
   workup.ADDITIONfollowed by the addition of acetonitrile (25 mL)
4. 4
   温度The reaction was heated
5. 5
   温度to reflux for 5 hours
6. 6
   温度After cooling
7. 7
   workup.ADDITIONthe reaction was diluted with ethyl acetate (200 mL)
8. 8
   ろ過filtered through CELITE diatomaceous earth
9. 9
   洗浄rinsed with copious amounts of ethyl acetate
10. 10
    洗浄The organic solution was washed twice with brine (50 mL)
11. 11
    乾燥dried over sodium sulfate
12. 12
    ろ過filtered through a fritted funnel
13. 13
    その他the volatiles were removed under vacuum
14. 14
    その他The crude residue was crystallized from methanol, which

実験手順

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.

出典