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

HRID 6813

반응식

HRID 6813 반응식
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[C-:13]#[N:14].[Na+]>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:12]=[C:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:13]#[N:14])[CH:3]=2)[NH:8]1

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 220189516-Iodo-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 152705762-Oxo-1,2,3,4-tetrahydroquinoline-6-carbonitrile

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc386eeb65804bc3a3674cae524f7269
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084156B2

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