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

HRID 1953341Notes

Reaction equation

HRID 1953341 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-ac50bcc031cd4276af1a2c768914c41a
Source dataset
uspto-grants-2000_09
Patent number
US06114536

Reaction notes

Loading…