Sodium hydride → 1-(2,2-Diethoxyethyl)-1H-indole-2,3-dione 3-(O-methyloxime)

HRID 618567Notes

Reaction equation

HRID 618567 reaction equation
[H-].[Na+].[CH3:3][O:4][N:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:15].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17]>CN(C)C=O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[N:5][O:4][CH3:3])[C:7]1=[O:15])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 136067498HCID 136067498, compound

Product 1

HCID 539421061-(2,2-Diethoxyethyl)-1H-indole-2,3-dione 3-(O-methyloxime)Yield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium hydride (prepared by washing 50 g of 60% oily sodium hydride with hexane) in 1 l of N,N-dimethylformamide was added dropwise a solution of 176 g of 3-methoxyiminoindolin-2-one in 3 l of N,N-dimethylformamide at 0° C. in a nitrogen stream. To the mixture were added 1 l of N,N-dimethylformamide and 330 ml of bromoacetaldehyde diethyl acetal, and the mixture was heated to 70° C., at which it was stirred for 45 hours. The reaction mixture was concentrated, and the concentrate was diluted with ethyl acetate and washed with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 284 g (97%) of 1-(2,2-diethoxyethyl)-3-methoxyiminoindolin-2-one.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe concentrate was diluted with ethyl acetate
  3. washwashed with an aqueous solution of sodium chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-560c645070e847b5a2f055cbcc7661fc
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

Loading…