[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH2:17][OH:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1>ClCCl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH:17]=[O:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1A little at a time, 3.90 g (44.9 mmol) of manganese(IV) oxide were added to a solution of 3.00 g (11.2 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylate in 162 mg of dichloromethane, and the mixture was stirred at 40° C. for 4 hours. After cooling to 20° C., a further 3.90 g (44.9 mmol) of manganese(IV) oxide were added, and the mixture was heated at 40° C. overnight. After cooling to 20° C., the mixture was filtered through Celite and the filtrate was freed from the solvent under reduced pressure.
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