Ethyl 2-cyanopyridine-3-carboxylate

557-21-1

1452-94-4

75358-90-6

To a solution of ethyl 2-chloropyridine-3-carboxylate (15.0 g, 81 mmol) in anhydrous N,N-dimethylacetamide (75 mL) was added zinc cyanide (5.71 g, 48.6 mmol), tris(dibenzylideneacetone)dipalladium (742 mg, 0.81 mmol), zinc powder (636 mg, 9.72 mmol), and 1,1'-bis(diphenylphosphinyl ) ferrocene (898 mg, 1.62 mmol). The reaction mixture was heated and stirred at 120 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and then partitioned between water (300 mL) and ether (150 mL). The organic and aqueous phases were separated by Celite filtration of the mixture. The aqueous phase was further extracted with ether (2 x 100 mL), all ether layers were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give ethyl 2-cyanonicotinate (14.26 g, 100% yield).