تفاعل #6909

معادلة التفاعل

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

sodium cyanide

→

title compound

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

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with a reflux condenser
2. 2
   أخرىpurge cycles
3. 3
   workup.ADDITIONfollowed by the addition of acetonitrile (25 mL)
4. 4
   درجة الحرارةThe reaction was heated
5. 5
   درجة الحرارةto reflux for 5 hours
6. 6
   درجة الحرارةAfter cooling
7. 7
   workup.ADDITIONthe reaction was diluted with ethyl acetate (200 mL)
8. 8
   ترشيحfiltered through CELITE diatomaceous earth
9. 9
   غسيلrinsed with copious amounts of ethyl acetate
10. 10
    غسيلThe organic solution was washed twice with brine (50 mL)
11. 11
    تجفيفdried over sodium sulfate
12. 12
    ترشيحfiltered through a fritted funnel
13. 13
    أخرىthe volatiles were removed under vacuum
14. 14
    أخرىThe crude residue was crystallized from methanol, which

الإجراء التجريبي

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.

المصدر