3-Acetylpyridine → 1-(3-Pyridinyl)ethanone oxime

HRID 2291835Notes

Reaction equation

HRID 2291835 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=O)[CH3:8])[CH:2]=1.Cl.[NH2:11][OH:12].C(=O)(O)[O-].[Na+]>CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[N:11][OH:12])[CH3:8])[CH:2]=1

Participants

6

Reactant 3

HCID 95893-AcetylpyridineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 222791-(3-Pyridinyl)ethanone oximeYield 99.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 50 g (0.41 mol) of 1-(3-pyridinyl)-ethanone and 29 g (0.42 mol) of hydroxylamine hydrochloride in 250 ml of methanol was heated under reflux for five hours. Upon cooling to room temperature, a white solid separated from the reaction mixture. This material was collected by filtration and the filtrate was concentrated to yield additional white solid. The combined solids were dissolved in water and the solution was made weakly basic by the addition of sodium bicarbonate solution while cooling. The white precipitate which formed was separated by filtration to yield 55.4 g of 1-(3-pyridinyl)ethanone oxime, mp 115°-117° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for five hours
  3. customa white solid separated from the reaction mixture
  4. filtrationThis material was collected by filtration
  5. concentrationthe filtrate was concentrated
  6. customto yield additional white solid
  7. temperaturewhile cooling
  8. customThe white precipitate which formed
  9. customwas separated by filtration

Sources & evidence

ORD record
ord-b8c84bf4026c49b4b0a5fd29ceb7d16e
Source dataset
uspto-grants-1989_01
Patent number
US04798841

Reaction notes

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