Phosphate → 2-Methoxy-5-(nitromethyl)pyridine
Reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1.C(#N)C.P([O-])([O-])([O-])=[O:16].S([O-])(O[O-])(=O)=O.[K+].[K+]>O.CC(C)=O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][N+:2]([O-:16])=[O:1])=[CH:5][N:6]=1Participants
Conditions
- Temperature
- 45 °C
Procedure
To a mixture of 2 g of N-hydroxy-1-(6-methoxypyridin-3-yl)methanimine, 50 ml of acetonitrile, and 50 ml of an aqueous phosphate buffer solution (pH 6.9) was added a mixed liquid of 20 g of potassium peroxymonosulfate (Oxone: 2KHSO5.KHSO4.K2SO4) in 50 ml water and 50 ml of acetone at room temperature, followed by stirring at 45° C. for 4 hours. The insoluble materials were separated by filtration and washed with diethyl ether. The organic layer was washed with a saturated aqueous sodium sulfite solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 251 mg of 2-methoxy-5-(nitromethyl)pyridine.
Workup
- customThe insoluble materials were separated by filtration
- washwashed with diethyl ether
- washThe organic layer was washed with a saturated aqueous sodium sulfite solution
- dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
- customthe solvent was then evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-e882be149f3e41d09377019c46af79cc
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278968B2
Reaction notes
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