Methanol → 1-(Pyridin-4-yl)propan-1-one oxime

HRID 2388193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388193
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].CO.[N:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH2:18][CH3:19])=[CH:13][CH:12]=1>CCOC(C)=O.O>[N:11]1[CH:16]=[CH:15][C:14]([C:17](=[N:2][OH:3])[CH2:18][CH3:19])=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 743431-(4-Pyridinyl)-1-propanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Produkt 1

HCID 1363417421-(Pyridin-4-yl)propan-1-one oximeAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Hydroxylamine hydrochloride (2.8 g, 40.7 mmol) and sodium acetate (3.3 g, 40.7 mmol) were added to 20 mL of methanol and the resulting white slurry was stirred at room temperature for 30 min. 1-(Pyridin-4-yl)propan-1-one (5.0 g, 37.0 mmol) was added and the mixture was stirred at room temperature for 20 hours. Water (50 mL) and EtOAc (50 mL) were added and the organic layer was separated. The aqueous layer was basified with solid sodium bicarbonate and extracted with additional EtOAc. The combined organic layer was washed with saturated NaHCO3 solution and dried over MgSO4. The solvent was evaporated in vacuo to give 5.3 g of the title compound. MS: (+) m/z 151.36 (M+1).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. customthe organic layer was separated
  3. extractionextracted with additional EtOAc
  4. washThe combined organic layer was washed with saturated NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0c22f94adf4d4ddcb6804d0d42b32305
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08269008B2

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