Sodium Cyanide → 2-Oxo-1,2,3,4-tetrahydroquinoline-6-carbonitrile

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.

1. customequipped with a reflux condenser
2. custompurge cycles
3. additionfollowed by the addition of acetonitrile (25 mL)
4. temperatureThe reaction was heated
5. temperatureto reflux for 5 hours
6. temperatureAfter cooling
7. additionthe reaction was diluted with ethyl acetate (200 mL)
8. filtrationfiltered through CELITE diatomaceous earth
9. washrinsed with copious amounts of ethyl acetate
10. washThe organic solution was washed twice with brine (50 mL)
11. dry with materialdried over sodium sulfate
12. filtrationfiltered through a fritted funnel
13. customthe volatiles were removed under vacuum
14. customThe crude residue was crystallized from methanol, which

ORD record

ord-dc386eeb65804bc3a3674cae524f7269

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084156B2