Triethylamine → 3-Fluoro-4-methylpyridine-2-carbonitrile

Participants

Reaction Steps

To a stirred solution of 0.95 g (7.48 mmol) of 3-fluoro-4-methylpyridine N-oxide 5-2 in 20 mL of acetonitrile was added 1.14 g (11.2 mmol) of triethylamine followed by 1.48 g (15.0 mmol) of trimethylsilyl cyanide. This reaction mixture was heated at reflux for 48 h, after which time the solution was concentrated at reduced pressure. The dark residue was dissolved in CHCl3, washed with saturated aqueous NaHCO3 and the aqueous layer back-washed with chloroform (4×). The combined organic layers were dried over MgSO4 and the solvents removed at reduced pressure to give an oil that was chromatographed on SiO2 using 75:25 hexane-EtOAc to give 5-3 as a yellow oil: 1H NMR (CDCl3) δ 8.39 (d, 1H, 4.8 Hz), 7.09 (br dd, 1H, 5.8, 5.8 Hz), 2.41 (s, 3H).

Provenance & Evidence