[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[C:14]([NH:16][CH3:17])[CH:13]=[CH:12][N:11]=1.C([O-])(=O)C.[K+]>CC(O)=O>[Cl:9][C:10]1[CH:15]=[C:14]([NH:16][CH3:17])[C:13]([Cl:1])=[CH:12][N:11]=1N-Chlorosuccinimide (0.623 g, 4.67 mmol) was added to 2-chloro-N-methyl-pyridin-4-amine (0.50 g, 3.89 mmol) and potassium acetate (0.763 g, 7.78 mmol) in AcOH (25 mL) and the mixture was stirred at 80° C. for 1.25 hours. The mixture was cooled and concentrated in vacuo. The concentrated mixture was diluted with water, neutralised with aqueous NaOH and extracted with EtOAc (×3). The organic extracts were evaporated onto silica gel. Gradient chromatography, eluting with 10-50% EtOAc:c-Hex, gave 2,5-dichloro-N-methylpyridin-4-amine (0.114 g, 0.699 mmol, 18% yield).
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