Hydrochloric Acid → 1-(3-Chloropyridin-2-yl)ethanone
Reaction equation
[Cl:1][C:2]1C(C#N)=[N:4][CH:5]=[CH:6][CH:7]=1.C([O:12][CH2:13][CH3:14])C.Cl.[CH2:16]1COCC1>>[C:13]([C:14]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=1)(=[O:12])[CH3:16]Participants
5
Procedure
Dissolve 3-chloro-2-cyanopyridine (10.0 g, 0.072 mol, Chem. Pharm. Bull. (1985) 33:565-571) in anhydrous THF (200 mL) under N2 atmosphere and cool in an ice bath. Add drop wise 3.0 M MeMgl in diethyl ether (48 ml, 0.14 mol) to the reaction mixture and stir in an ice bath for 2 hours. Pour the reaction mixture over ice cold water, acidify the mixture with 2.0 N aq. HCl to pH 2 to 3. Extract the reaction mixture with EtOAc (3×100 mL) and dry over anhydrous MgSO4. Filter, concentrate under vacuum and then filter through a pad of silica gel using 20% ethyl acetate/hexane as eluent. Removal of solvent under reduced pressure gives pure 2-acetyl-3-chloropyridine as oil.
Workup
- temperaturecool in an ice bath
- additionPour the reaction mixture over ice cold water
- extractionExtract the reaction mixture with EtOAc (3×100 mL)
- dry with materialdry over anhydrous MgSO4
- filtrationFilter
- concentrationconcentrate under vacuum
- filtrationfilter through a pad of silica gel using 20% ethyl acetate/hexane as eluent
- customRemoval of solvent under reduced pressure
Sources & evidence
- ORD record
- ord-9baff1f9762947f78bec357af27b36b8
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074799B2
Reaction notes
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