Methyl 2-pyridylacetate → methyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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.