2-Chloro-N-methoxy-N-methylnicotinamide → 1-(2-Chloropyridin-3-YL)propan-1-one
Reaction equation
[Cl:1][C:2]1[C:7]([C:8](N(OC)C)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C[Mg]Br.[CH2:17](OCC)[CH3:18]>C1COCC1.Cl>[Cl:1][C:2]1[C:7]([C:8](=[O:9])[CH2:17][CH3:18])=[CH:6][CH:5]=[CH:4][N:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
2-Chloro-N-methoxy-N-methylpyridine-3-carboxamide (1.0 g) was dissolved in THF (30 ml), 3 Methylmagnesium bromide-diethyl ether solution (2.0 ml) was added dropwise at room temperature, and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was diluted with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (630 mg).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed successively with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-2504eaf62c4044e7af3a87aaee74375b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029388B2
Reaction notes
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