Hydroxyamine hydrochloride → HCID 136342797, compound

HRID 868231Notes

Reaction equation

HRID 868231 reaction equation
Cl.[NH2:2][OH:3].[CH2:4]([C:6]([CH:13]([N+:15]([O-:17])=[O:16])[CH3:14])=[CH:7][C:8](=[N:11][OH:12])[CH:9]=O)[CH3:5]>C(Cl)(Cl)Cl.CO>[CH2:4]([C:6]([CH:13]([N+:15]([O-:17])=[O:16])[CH3:14])=[CH:7][C:8](=[N:11][OH:12])[CH:9]=[N:2][OH:3])[CH3:5]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86257292HCID 86257292, compound

Product 1

HCID 136342797HCID 136342797, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Hydroxylamine hydrochloride (69.5 mg) was added to a solution of 4-ethyl-2-hydroxyimino-5-nitro-3-hexenal (100 mg) in a mixture of chloroform (3 ml) and methanol (2 ml) with stirring at room temperature. The resulting mixture was stirred at the same temperature overnight and evaporated to dryness. The residue was washed successively with water, aqueous sodium bicarbonate solution and brine, and dried over magnesium sulfate. The solvent was distilled under reduced pressure to give a residue which was purified by preparative thin layer chromatography [solvent:methanol-chloroform (10:90)] to give 4-ethyl-2-hydroxyimino-5-nitro-3-hexenaldehyde oxime (65 mg).

Workup

  1. stirringThe resulting mixture was stirred at the same temperature overnight
  2. customevaporated to dryness
  3. washThe residue was washed successively with water, aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled under reduced pressure
  6. customto give a residue which
  7. customwas purified by preparative thin layer chromatography [solvent:methanol-chloroform (10:90)]

Sources & evidence

ORD record
ord-2d28afc1093749e381391ad8d30b9e03
Source dataset
uspto-grants-1988_10
Patent number
US04778804

Reaction notes

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