Dimethylcarbamoyl Chloride → Methyl 2-cyanopyridine-4-carboxylate

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Trimethylsilyl cyanide (3.8 g, 0.0386 mol) and dimethylcarbamyl chloride (5.0 g, 0.0483 mol) were added to a solution of methylisonicotinate N-oxide (5.0 g, 0.0322 mol) in dry CH2Cl2 (50 mL) at room temperature. The reaction mixture was stirred at room temperature for 12 h and then quenched with 10% K2CO3 solution. The organic product was extracted with CH2Cl2 and the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica 230-400 mesh, eluent 1-2% MeOH in CH2Cl2) to afford methyl 2-cyanoisonicotinate (1.75 g, yield 33%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.97-8.95 (d, J=5.0 Hz, 1H), 8.41 (m, 1H), 8.15-8.13 (dd, J=4.8 Hz, 1.6 Hz, 1H), 3.92 (s, 3H).

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