Hydroxylamine HCl → Methyl 2-((5-(1-(hydroxyimino)ethyl)pyridin-2-yl)oxy)acetate

HRID 68310

Reaction equation

HRID 68310 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:8][CH:9]=1)(=O)[CH3:2].C([O-])(=O)C.[Na+].[Cl-].[OH:22][NH3+:23]>C(O)C.O>[OH:22][N:23]=[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 68281905Methyl 2-((5-acetylpyridin-2-yl)oxy)acetate

Product 1

HCID 86699620Methyl 2-((5-(1-(hydroxyimino)ethyl)pyridin-2-yl)oxy)acetateYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-((5-acetylpyridin-2-yl)oxy)acetate (1.23 gm, 0.059 mole) in ethanol (10 mL), a solution of sodium acetate (0.942 gm, 0.0117 mole) and hydroxylammonium chloride (1.2 gm, 0.0117 mole) in water (5 ml) was added and the reaction mixture was refluxed for 1 h. The reaction mixture was coiled to room temperature and solvent was evapourated in vacuum. The residue was diluted with ice cold water and solid seperated was filtered, washed with water and dried over P2O5 under vacuum to yield 1.15 gm (88%) of title product as off white solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 1 h
  2. customwas coiled to room temperature
  3. additionThe residue was diluted with ice cold water and solid
  4. customseperated
  5. filtrationwas filtered
  6. washwashed with water
  7. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-c52054b585b049c482cb8432945af5a3
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Linked notes

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