Allyl bromide → 1-Allyl-3,3-dimethoxyindolin-2-one

HRID 618529Notes

Reaction equation

HRID 618529 reaction equation
[CH3:1][O:2][C:3]1([O:13][CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12].[H-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C)C=O>[CH2:19]([N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([O:13][CH3:14])([O:2][CH3:1])[C:4]1=[O:12])[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 154807453,3-Dimethoxy-1,3-dihydro-2H-indol-2-one

Product 1

HCID 220131101-Allyl-3,3-dimethoxyindolin-2-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.86 g of 3,3-dimethoxyindolin-2-one in 30 ml of N,N-dimethylformamide was added dropwise to a suspension of 1.2 g of sodium hydride (60%) in 40 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After the mixture was stirred at that temperature for 30 minutes, 2.60 ml of allyl bromide was added thereto. The resulting mixture was stirred for 1 hour and then concentrated. Chloroform was added to the residue, and the mixture was washed with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting crude product was purified by silica gel column chromatography (chloroform/hexane=1/1) to give 4.19 g (90%) of the title compound.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour
  2. concentrationconcentrated
  3. additionChloroform was added to the residue
  4. washthe mixture was washed with an aqueous solution of sodium chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatography (chloroform/hexane=1/1)

Sources & evidence

ORD record
ord-acd1897ca1d64a8281aee22b26abe769
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

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