[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].S(=O)(=O)(O)O.[O:26]=[C:27](C)[CH2:28]C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O.[N+]([O-])([O-])=O.[Ag+]>[C:27]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=1)[C:1]#[N:8])(=[O:26])[CH3:28]To a solution of isonicotinonitrile (52 g, 0.5 mol) in dichloromethane (1300 mL) and water (1100 mL) were added ammonium persulfate ((NH4)2S2O8) (170 g, 0.75 mol), silver nitrate (6.8 g, 0.04 mol) and aqueous sulfuric acid (40 mL, 98% sulfuric acid in 400 mL). A solution of 3-oxo-butyric acid (110 g, 1.25 mol) in dichloromethane (100 mL) was added dropwise while keeping the mixture refluxing. The reaction mixture was refluxed for 2 h. The resulting mixture was basified to pH˜8-9 using sodium carbonate powder. The mixture was filtered and the filtrate was extracted with dichloromethane (500 mL×3). The combined organics were dried over sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to afford 2-acetylisonicotinonitrile (52.0 g, 71.9%).
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