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

HRID 1441161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441161
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9ce2bb72cde84e2e9f052f8e0df1b5c5
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05502252

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