4-Acetylpyridine → N-[1-(Pyridin-4-yl)ethylidene]hydroxylamine

HRID 1995065Notes

Reaction equation

HRID 1995065 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].[C:7]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)(=O)[CH3:8]>CO>[C:7](=[N:2][OH:3])([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[CH3:8]

Participants

5

Reactant 3

HCID 142824-AcetylpyridineHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 247997N-[1-(Pyridin-4-yl)ethylidene]hydroxylamineYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 7.64 g. (110 mmole) of hydroxylamine hydrochloride in 150 ml. of methyl alcohol were added 5.94 g. (110 mmole) of sodium methylate and the mixture was stirred at room temperature for 10 minutes. A solution of 12.11 g. (110 mmoles) of 4-acetylpyridine in 50 ml. of methyl alcohol was added dropwise over 3 minutes and the reaction mixture was stirred at room temperature for 3 hours and at the reflux temperature for 2.5 hours. After the mixture had cooled, the precipitate of sodium chloride was separated by filtration and the filtrate was concentrated by evaporation to one-half of the original volume. The concentrate was diluted with 50 ml. of water and the solution concentrated to a volume of about 100 ml. This concentrate was chilled in an ice bath for 30 minutes and the precipitate of the oxime was separated by filtration in the cold. There were obtained 8.38 g. (61.5% yield) of 4-acetylpyridine oxime.

Workup

  1. temperatureAfter the mixture had cooled
  2. customthe precipitate of sodium chloride was separated by filtration
  3. concentrationthe filtrate was concentrated by evaporation to one-half of the original volume
  4. additionThe concentrate was diluted with 50 ml
  5. concentrationof water and the solution concentrated to a volume of about 100 ml
  6. temperatureThis concentrate was chilled in an ice bath for 30 minutes
  7. customthe precipitate of the oxime was separated by filtration in the cold
  8. customThere were obtained 8.38 g

Sources & evidence

ORD record
ord-74e4c1bfb8224690af2002e6a0b81858
Source dataset
uspto-grants-1983_09
Patent number
US04402955

Reaction notes

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