1,4-Dioxane → (5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)Oxoacetamide

HRID 351585노트

반응식

HRID 351585 반응식
[C:1]1([CH2:13][C:14]([NH2:16])=[O:15])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[O:17]1CCOCC1>O.[Pd]>[C:1]1([C:13](=[O:17])[C:14]([NH2:16])=[O:15])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

참가 물질

5

반응물 2

HCID 312751,4-DioxaneHCID 16742967(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)acetamide

생성물 1

HCID 22556693(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)Oxoacetamide수율 96%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 962Water용매

실험 절차

To a solution of (5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)acetamide (0.30 g, 1.31 mmol) in dioxane (6 mL) and water (2 mL) was added 10% palladium on carbon (0.060 g), followed by the careful addition of NaH2PO2.H2O (0.60 g, 5.67 mmol) and the reaction was brought to reflux under nitrogen. After 3 hours an additional 0.60 g of NaH2PO2.H2O was added and the reaction was heated at reflux for another 6 hrs. The mixture was cooled, filtered through a pad of Celite, and washed well with ethyl acetate (100 mL). The solution was concentrated under reduced pressure and the residue triturated with water (20 mL). The resulting suspension was filtered and the recovered solid dried under reduced pressure to provide 0.27 g (96%) of the title compound as a white solid.

후처리

  1. temperatureto reflux under nitrogen
  2. temperaturethe reaction was heated
  3. temperatureat reflux for another 6 hrs
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through a pad of Celite
  6. washwashed well with ethyl acetate (100 mL)
  7. concentrationThe solution was concentrated under reduced pressure
  8. customthe residue triturated with water (20 mL)
  9. filtrationThe resulting suspension was filtered
  10. customthe recovered solid dried under reduced pressure

출처 및 근거

ORD 기록
ord-4a9d35e15e5a4c568e6a1f5fb0f5cde0
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743785B2

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