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

HRID 2388193Notes

Reaction equation

HRID 2388193 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 1363417421-(Pyridin-4-yl)propan-1-one oximeYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0c22f94adf4d4ddcb6804d0d42b32305
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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