[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)(=[O:10])[CH3:9]A mixture of 1-(6-chloro-2-pyridyl)ethanol (2.13 g) and manganese dioxide (8.4 g) in chloroform (21 ml) was refluxed for 8 hours. After cooling, the mixture was filtered through celite pad and the filtrate was evaporated in vacuo. The residue was purified by distillation under reduced pressure to give 2-acetyl-6-chloropyridine (1.84 g).
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