Acetic Acid → (E)-4-ethyl-2-methoxyimino-5-nitro-3-hexenamide

HRID 868229Notes

Reaction equation

HRID 868229 reaction equation
[CH2:1](/[C:3](/[CH:11]([N+:13]([O-:15])=[O:14])[CH3:12])=[CH:4]\[C:5](=[N:9][OH:10])[C:6]([NH2:8])=[O:7])[CH3:2].[N+](=[CH2:18])=[N-].C(O)(=O)C>CO>[CH2:1](/[C:3](/[CH:11]([N+:13]([O-:15])=[O:14])[CH3:12])=[CH:4]\[C:5](=[N:9][O:10][CH3:18])[C:6]([NH2:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 86742405(E)-4-ethyl-2-hydroxyimino-5-nitro-3-hexenamide

Product 1

HCID 86742404(E)-4-ethyl-2-methoxyimino-5-nitro-3-hexenamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (E)-4-ethyl-2-hydroxyimino-5-nitro-3-hexenamide (37 mg) in methanol (5 ml) was added excess etheral diazomethane at -20° C. The resulting mixture was allowed to stand at 0° C. for an hour and then acetic acid was added thereto until the yellow color of the solution was discharged. The resulting reaction mixture was evaporated under reduced pressure to give an oil which was purified by preparative thin layer chromatography, developing with chloroform containing 5% methanol to give (E)-4-ethyl-2-methoxyimino-5-nitro-3-hexenamide (21.5 mg).

Workup

  1. waitto stand at 0° C. for an hour
  2. customThe resulting reaction mixture
  3. customwas evaporated under reduced pressure
  4. customto give an oil which
  5. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-d26d0d9c34ba449291067e49f637a27a
Source dataset
uspto-grants-1988_10
Patent number
US04778804

Reaction notes

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