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

HRID 351585ノート

反応式

HRID 351585 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a9d35e15e5a4c568e6a1f5fb0f5cde0
出典データセット
uspto-grants-2004_06
特許番号
US06743785B2

反応ノート

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