Water → 1-(2,6-Difluoropyridin-3-yl)ethanone oxime

HRID 1436099Notes

Reaction equation

HRID 1436099 reaction equation
S(O)(O)(=O)=O.[NH2:6][OH:7].C([O-])(=O)C.[Na+].[F:13][C:14]1[C:19]([C:20](=O)[CH3:21])=[CH:18][CH:17]=[C:16]([F:23])[N:15]=1.O>C1COCC1.C(OCC)(=O)C>[F:13][C:14]1[C:19]([C:20](=[N:6][OH:7])[CH3:21])=[CH:18][CH:17]=[C:16]([F:23])[N:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium AcetateHCID 251322441-(2,6-Difluoropyridin-3-yl)ethanone

Product 1

HCID 866126081-(2,6-Difluoropyridin-3-yl)ethanone oximeYield 53.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydroxylamine sulfate (13.1 g) and sodium acetate (10.9 g) were added to a solution of 1-(2,6-difluoropyridin-3-yl)ethanone (4.18 g) in aqueous THF (50%, 200 mL), and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate) to obtain 2.44 g of the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-a75dc279982e41d9862c702a9f9fe17a
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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