Methanol → N-methyl-2-(2-methylphenyl)-2-hydroxyiminoacetamide

HRID 1441161Notes

Reaction equation

HRID 1441161 reaction equation
[CH3:1][NH:2][C:3](=[O:13])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=O.CO.Cl.[NH2:17][OH:18]>O>[CH3:1][NH:2][C:3](=[O:13])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[N:17][OH:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 15239356N-methyl-2-(2-methylphenyl)-2-oxoacetamide

Product 1

HCID 73792991N-methyl-2-(2-methylphenyl)-2-hydroxyiminoacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-methyl-2-(2-methylphenyl)-2-oxoacetamide (5.31 g, 0.03 mol), added were methanol (30 ml) and hydroxylamine hydrochloride (4.17 g, 0.06 ml), and the reaction mixture was heated under reflux for 5 hours. After completion of the reaction, water (150 ml) was added to the reaction mixture which was then extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give N-methyl-2-(2-methylphenyl)-2-hydroxyiminoacetamide in E-form (4.79 g; yield, 83.1%) and Z-form (0.50 g; yield, 8.7%) as colorless crystals.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5 hours
  3. additionwas added to the reaction mixture which
  4. extractionwas then extracted with methylene chloride
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-9ce2bb72cde84e2e9f052f8e0df1b5c5
Source dataset
uspto-grants-1996_03
Patent number
US05502252

Reaction notes

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