Methanol → 2-Methoxy-4-methyl-5-nitropyridine

Participants

Reaction Steps

To a stirred solution of sodium (2.30 g, 100mmol, 3.8 eq) in absolute methanol (75 ml) at 0° C., a solution of 2-chloro-4-methyl-5-nitropyridine (4.50 g, 26.07 mmol) in absolute methanol (15 ml) was added dropwise rapidly. The resulting dark colored solution was stirred at room temperature for 30 minutes, and then it was concentrated to a solid via evaporation under reduced pressure. This solidwas placed in water (25 ml), the pH of which was adjusted to 6 with concentrated HCl, and this aqueous mixture was extracted with ethyl acetate (2×25 ml). These extracts were combined, dried (MgSO4),and evaporated under reduced pressure to yield 2-methoxy-4-methyl-5-nitropyridine (4.30 g, 25.57 mmol, 98%) as an orange solid: mp, 70°-72° C.; 1H NMR (DMSO-d6) δ 8.94 (s, 1H), 6.97 (s, 1H), 3.99 (s, 3H), 2.58 (s, 3H); LRMS (m/z relativeintensity) 168 (M+, 98), 167 (100), 151 (34), 138 (24), 80 (17).

Provenance & Evidence