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

HRID 1460958Notes

Reaction equation

HRID 1460958 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-ee4e76eed61244b092fe8ff3e151be13
Source dataset
uspto-grants-1991_12
Patent number
US05073561

Reaction notes

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