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

HRID 546564Notes

Reaction equation

HRID 546564 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+]>CN(C)C=O.[Cl-].C([N+](CC)(CC)CC)C.O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[C:12]([N:11]1[C:3]2[C:2](=[CH:7][CH:6]=[C:5]([N+:8]([O-:10])=[O:9])[CH:4]=2)[C:16]([CH3:18])([CH3:17])[CH2:15]1)(=[O:14])[CH3:13]

Participants

8

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 77.1%

Reagents, catalysts & solvents 4

HCID 5946Tetraethylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.2 g of N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide obtained in stage d) below in 140 mL of dimethylformamide are added 2.12 g of N,N,N-triethylethanaminium chloride, 1.4 g of sodium formate and 3.4 g of sodium acetate. After stirring for 30 minutes under argon at room temperature, 410 mg of palladium diacetate are added and the mixture is heated at 80° C. for 5 hours. After cooling to room temperature, the reaction mixture is diluted with one litre of water, and the solid formed is filtered off and washed with four times 40 mL of water. The solid is then dissolved in 200 mL of ethyl acetate, dried over magnesium sulphate in the presence of 0.5 g of vegetable charcoal, filtered and concentrated under reduced pressure to give 3 g of 1-acetyl-3,3-dimethyl-6-nitroindoline in the form of a beige-yellow solid, the characteristics of which are as follows:

Workup

  1. temperaturethe mixture is heated at 80° C. for 5 hours
  2. temperatureAfter cooling to room temperature
  3. customthe solid formed
  4. filtrationis filtered off
  5. washwashed with four times 40 mL of water
  6. dissolutionThe solid is then dissolved in 200 mL of ethyl acetate
  7. dry with materialdried over magnesium sulphate in the presence of 0.5 g of vegetable charcoal
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca8e8dc1ed7d4992a78a6d9351261f43
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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