2-Chloronicotinic acid → 3-Acetyl-2-chloropyridine
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:11][Mg]Br>C1COCC1>[Cl:1][C:2]1[C:3]([C:4](=[O:6])[CH3:11])=[CH:7][CH:8]=[CH:9][N:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-chloronicotinic acid (B-1) (7.88 g, 50.0 mmol) in THF (100 mL) was added methyl magnesium bromide (42 mL, 3-Methyl ether solution) dropwise under 0° C. Upon completion of the addition, the reaction mixture was stirred at 0° C. for 0.5 h and then at room temperature overnight. The reaction mixture was added into ice/water (150 mL), and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated to afford the title compound 1-(2-chloropyridin-3-yl)ethanone (B-2). MS (m/z): 156 (M+1)+.
Workup
- additionUpon completion of the addition
- customat room temperature
- customovernight
- extractionextracted with ethyl acetate
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5852800fd5874b948515e3f651c119eb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507487B2
Reaction notes
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