Hydroxyamine hydrochloride → 1-(5-(Prop-1-en-2-yl)pyridin-3-yl)ethanone oxime

HRID 2071020Notes

Reaction equation

HRID 2071020 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:10](=O)[CH3:11])[CH:7]=[N:8][CH:9]=1)[CH3:3].[NH2:13][OH:14].Cl>CCO.O.[OH-].[Na+]>[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:10](=[N:13][OH:14])[CH3:11])[CH:7]=[N:8][CH:9]=1)[CH3:3]

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 686706051-(5-(Prop-1-en-2-yl)pyridin-3-yl)ethanone

Product 1

HCID 866474221-(5-(Prop-1-en-2-yl)pyridin-3-yl)ethanone oximeYield 79.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanone (460 mg, 2.86 mmol) in 95% EtOH was added a solution of NH2OH.HCl (1.19 g, 17.14 mmol) in a mixture of water (5.8 mL) and 10% NaOH (5.8 mL) and refluxed for 2.5 h. All solvent was removed. The residue was dissolved in CHCl3, washed with water, dried with Na2SO4 and concentrated under reduced pressure to yield 400 mg of crude 1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanone oxime.

Workup

  1. temperaturerefluxed for 2.5 h
  2. customAll solvent was removed
  3. dissolutionThe residue was dissolved in CHCl3
  4. washwashed with water
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e147ab0d50b442a9884cffd846ce1bdc
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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