Sodium hydride → HCID 22013032, compound

HRID 365983Notes

Reaction equation

HRID 365983 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+].[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH2:20]Br>CN(C)C=O>[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)[N:5]([CH2:20][CH:19]([O:22][CH3:23])[O:18][CH3:17])[C:4]1=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 154807453,3-Dimethoxy-1,3-dihydro-2H-indol-2-one

Product 1

HCID 22013032HCID 22013032, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 34.3 g of 3,3-dimethoxyindolin-2-one in 400 ml of N,N-dimethylformamide was added dropwise to a suspension of 8.56 g of sodium hydride (60%) in 100 ml of N,N-dimethylformamide at 0° C. in a nitrogen stream. After the mixture was stirred at that temperature for 30 minutes, 36.2 g of bromoacetaldehyde dimethyl acetal was added thereto. The resulting mixture was stirred at 80° C. for 1 day and then concentrated. Ethyl acetate 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 recrystallized from isopropyl alcohol/hexane to give 25.1 g (50%) of the title compound.

Workup

  1. stirringThe resulting mixture was stirred at 80° C. for 1 day
  2. concentrationconcentrated
  3. additionEthyl acetate 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 recrystallized from isopropyl alcohol/hexane

Sources & evidence

ORD record
ord-e827145266f1426494f8109d96be3648
Source dataset
uspto-grants-2000_10
Patent number
US06127544

Reaction notes

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