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

HRID 365982Notes

Reaction equation

HRID 365982 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-28251f226699450aac1f05d136722b9c
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

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