[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[OH:10][C:11]1[CH:18]=[C:17]([CH3:19])[C:14]([C:15]#[N:16])=[C:13]([CH3:20])[N:12]=1.[OH-].[Na+]>O>[OH:10][C:11]1[C:18]([N+:1]([O-:4])=[O:2])=[C:17]([CH3:19])[C:14]([C:15]#[N:16])=[C:13]([CH3:20])[N:12]=1To a stirring mixture of nitric acid (fuming, 36 mL) and sulfuric acid (18 mL) was added 6-hydroxy-2,4-dimethylnicotinonitrile (step 1, 9.0 g, 60.8 mmol) in one portion, and the mixture was stirred at room temperature. After 1 h, the mixture was poured in water (100 mL) and neutralized with 2N aqueous NaOH. The resulting precipitates were collected by filtration to afford 3.2 g (27%) of the title compound: 1H-NMR (DMSO-d6) δ 2.28 (3H, s), 2.11 (3H, s).
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