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

HRID 238507Notes

Reaction equation

HRID 238507 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+].CC([O-])=O.[Na+]>CN(C=O)C.[Cl-].C([N+](CC)(CC)CC)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

6

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)ethanone

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-(2-Bromo-5-nitrophenyl)-N-(2-methylprop-2-enyl)acetamide (4.5 g, Step B) was dissolved in anhydrous DMF (50 mL), tetraethyl-ammonium chloride (2.5 g), sodium formate (1.2 g), NaOAc (3 g) were added, and the resulting mixture was bubbled with N2 gas for 10 min. Pd(OAc)2 (350 mg) was added and the mixture was heated at 80° C. under N2 atmosphere overnight. After the mixture was concentrated in vacuo, it was partitioned between saturated NaHCO3 solution and EtOAc, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 2:1 Hexane:EtOAc to afford the title compound as a yellow gum. MS: 235 (M+1). Calc'd. for C12H14N2O3—234.25.

Workup

  1. customthe resulting mixture was bubbled with N2 gas for 10 min
  2. additionPd(OAc)2 (350 mg) was added
  3. concentrationAfter the mixture was concentrated in vacuo, it
  4. customwas partitioned between saturated NaHCO3 solution and EtOAc
  5. dry with materialthe resulting organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography on silica gel with 2:1 Hexane

Sources & evidence

ORD record
ord-77e73ded9b824a66be226629010b3db3
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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