Potassium Carbonate → 2-(3-nitropyridin-2-yl)acetonitrile

Participants

Reaction Steps

Using the procedure of R. B. Katz, M. Voyle, Synthesis, 314-316 (1989), a mixture of 2-chloro-3-nitro-pyridine (9.51 g, 60 mmol), K2CO3 (20.7 g, 150 mmol) and t-butyl cyanoacetate (13.0 mL, 90 mmol) in THF is heated at reflux temperature for 24 h, cooled and concentrated in vacuo. The residue is suspended in 1:1 water/CH2Cl2 and carefully acidified to pH 1 with concentrated hydrochloric acid. The layers are separated and the organic layer is dried over MgSO4 and concentrated in vacuo to a dark oil. This oil is treated with p-toluene-sulfonic acid monohydrate (1.0 g) and toluene, heated at reflux temperature for 2 h, cooled and decanted. The dark residue is washed with CH2Cl2. The combined CH2Cl2 washes and toluene superinnate are washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo to an oily solid. Trituration with 20:80 ethyl acetate:hexanes gives the title compound as an orange-brown solid, 6.50 g, (66% yield), mp 106-108° C., identified by NMR and mass spectral analyses.

Provenance & Evidence