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

HRID 351585Notes

Reaction equation

HRID 351585 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4a9d35e15e5a4c568e6a1f5fb0f5cde0
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Reaction notes

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