Methyl 2-pyridylacetate → methyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate

HRID 1409546Notes

Reaction equation

HRID 1409546 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[N:12]([O-])=[O:13].[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:11][O:10][C:8](=[O:9])[C:7](=[N:12][OH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 74264Methyl 2-pyridylacetateHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 135778783methyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 2-pyridylacetate (3.78 g) in acetic acid (15 mL) was added dropwise an aqueous solution (5 mL) of sodium nitrite (1.75 g) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was neutralized with an aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=75/25 to 25/75) to give methyl(hydroxyimino)(2-pyridyl)acetate (3.72 g, yield: 83%) as a colorless solid.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=75/25 to 25/75)

Sources & evidence

ORD record
ord-68cbbc9a54f0449992c8b093a26ec351
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Reaction notes

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