Methanol → 1-(2-Methyl-pyridin-4-yl)-ethanone oxime
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH3:10])[CH:5]=1)(=O)[CH3:2].Cl.[NH2:12][OH:13].CO.O.O.O.C([O-])(=O)C.[Na+]>O.[Cl-].[Na+].O>[CH3:10][C:6]1[CH:5]=[C:4]([C:1](=[N:12][OH:13])[CH3:2])[CH:9]=[CH:8][N:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a stirred suspension of 4-acetyl-2-methyl-pyridine [CAS No. 2732-28-7] (9.7 g, 71.8 mmol) in water (115 ml) was added at room temperature hydroxylamine hydrochloride (8.48 g, 122 mmol) and the mixture was heated to 70° C. At this temperature methanol (145 ml) was added dropwise over a period of 15 min and afterwards a solution of sodium acetate trihydrate (25.4 g, 187 mmol) in water (115 ml) was added dropwise over a period of 15 min. The reaction mixture was stirred at 80° C. for 3.5 h, brine (150 ml) was added and the solution was extracted with ethyl acetate (2×250 ml). The combined organic layers were washed with brine (150 ml), dried (MgSO4) and evaporated. The crude product was purified by crystallization from ethyl acetate/hexane to give 1-(2-methyl-pyridin-4-yl)-ethanone oxime (7.25 g, 67%) as an off-white solid; mp 154° C.
Workup
- extractionthe solution was extracted with ethyl acetate (2×250 ml)
- washThe combined organic layers were washed with brine (150 ml)
- dry with materialdried (MgSO4)
- customevaporated
- customThe crude product was purified by crystallization from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-b77cabe33af04792a1dd03c65ea168da
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514443B2
Reaction notes
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