Water → methyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate

HRID 1040457Notes

Reaction equation

HRID 1040457 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[N:12]([O-])=[O:13].[Na+].O>CC(O)=O>[CH3:1][O:2][C:3](=[O:11])[C:4](=[N:12][OH:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 74264Methyl 2-pyridylacetateHCID 23668193Sodium Nitrite

Product 1

HCID 135778783methyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetateYield 9,755.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of pyridin-2-yl-acetic acid methyl ester (8.9 ml, 0.66 mmol) in AcOH (16 mL) at 0° C. with stirring, an aqueous solution of sodium nitrite (4.67 g, 0.66 mmol in 14 mL) was added portion wise. After addition was completed stirring was continued for 40 min at room temperature. Water (30 mL) was added and the mixture was stirred for additional 1 h. The mixture was concentrated to remove most of the AcOH and basidified to pH 8˜9 with Na2CO3 aq. extracted with EtOAc (3×). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. Drying in a vacuum oven affords Hydroxyimino-pyridin-2-yl-acetic acid methyl ester (11.6 g, 97%) as an off-white solid, m/z 181.6 [M+1]+

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred for additional 1 h
  3. concentrationThe mixture was concentrated
  4. customto remove most of the AcOH and basidified to pH 8˜9 with Na2CO3 aq.
  5. extractionextracted with EtOAc (3×)
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customDrying in a vacuum oven

Sources & evidence

ORD record
ord-3d430fd540f8455f824aa05a55b23be0
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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