6-Carbamoylpyridine-2-carboxylic acid → 6-Cyanopyridine-2-carboxylic acid

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Reaction Steps

6-Carbamoylpicolinic acid (1.0 g, 6.0 mmol) was taken in phosphorus oxychloride (20 mL) and heated to reflux for 4 h. Excess POCl3 was removed under reduced pressure and the residue was quenched with ice water. The organic product was extracted with EtOAc and the solvent was removed under reduced pressure to afford 6-cyanopicolinic acid (500 mg, yield 56%), which was carried through without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.31-8.28 (m, 2H), 8.26-8.21 (m, 1H). MS (ESI) m/z: Calculated for C7H4N2O2: 148.03. found: 147.2 (M−H)−.

Provenance & Evidence