COC1C=C(OC)C=C[C:4]=1[CH2:5][NH:6][C:7]1[N+:8]([O-:17])=[CH:9][C:10]([CH3:16])=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1.C(OC(=O)C)(=[O:26])C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:16][C:10]1[C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]([NH:6][C:5](=[O:26])[CH3:4])=[N+:8]([O-:17])[CH:9]=1A solution of N-(2,4-dimethoxybenzyl)-5-methyl-4-nitropyridin-2-amine 1-oxide (1.1 g, 3.5 mmol) in DCM (20 mL) and TFA (3 mL) was allowed to stir at rt for 4 h. The reaction mixture was concentrated and the residue was dissolved in DCM (20 mL). To this solution were added TEA (2.5 mL, 17.7 mmol) and acetic anhydride (0.4 g, 4.3 mmol). The reaction mixture was allowed to stir at rt overnight and then filtered to give N-(5-methyl-4-nitro-1-oxidopyridin-2-yl)acetamide (0.73 g, 98%) which was used without further purification.
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