3-methyl-1-oxidopyridin-1-ium-2-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Methylpyridine-2-carbonitrile 1-oxide (8.42 g, 62.8 mmol) was stirred in refluxing POCl3 (60 mL, 646 mmol) for 6 hours. The mixture was cooled to room temperature and slowly poured into ice-water. The resulting beige precipitate was collected by filtration to give the title compound. The resulting beige precipitate was collected by filtration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Methylpyridine-2-carbonitrile (10 g, 85 mmol) was taken up in DCM (180 mL) and mCPBA (20.9 g, 93 mmol) was added. The resulting mixture was stirred at room temperature overnight. Additional mcpba (9.49 g, 42 mmol) was added and stirring continued at room temperature for 24 hours. Saturated aqueous NaHCO3 and the resulting mixture was extracted with EtOAc (3×), followed by 20% MeOH—CHCl3 (2×). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-20% MeOH/EtOAc) gave the title compound as a white solid. Additional mcpba (9.49 g, 42 mmol) was added stirring continued at room temperature for 24 hours Saturated aqueous NaHCO3 and the resulting mixture was extracted with EtOAc (3×) The combined organic extracts were dried over MgSO4 filtered concentrated in vacuo Purification of the residue by silica gel chromatography (0-20% MeOH/EtOAc)