Sodium Acetate → 1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

HRID 401388Notes

Reaction equation

HRID 401388 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:12](=[O:14])[CH3:13].C([O-])=O.[Na+].C([O-])(=O)C.[Na+]>O.[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:17][C:16]1([CH3:18])[C:2]2[C:3](=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[N:11]([C:12](=[O:14])[CH3:13])[CH2:15]1

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 2723810Sodium FormateHCID 21959573N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide

Product 1

HCID 161274181-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanoneYield 88%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 16211205Tetraethylammonium chloride monohydrateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-enyl)acetamide (3.1 g, 10.2 mmol), tetraethylammonium chloride hydrate (2.4 g, 149 mmol), sodium formate (1.08 g, 18 mmol), sodium acetate (2.76 g, 34.2 mmol) and palladium acetate (0.32 g, 13.2 mmol) in anhydrous DMF (50 mL) was stirred at 80° C. for 15 h under N2 atmosphere. After cooling, the mixture was filtered through Celite. The Celite was washed with EtOAc and the combined filtrates were washed with sat. NaHCO3. The separated organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure to provide 1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone as a brown solid (2.1 g, 88%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through Celite
  3. washThe Celite was washed with EtOAc
  4. washthe combined filtrates were washed with sat. NaHCO3
  5. washThe separated organic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98644ab522d74a2089080845fe34b7ff
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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