Sodium hydride → HCID 22013032, compound

HRID 1533704Notes

Reaction equation

HRID 1533704 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-cd9f523364ce46bf99f592faa198ba2c
Source dataset
uspto-grants-2001_03
Patent number
US06207836B1

Reaction notes

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