2-Chloro-3-methyl-5-nitropyridine → 2-Methoxy-3-methyl-5-nitropyridine

Participants

Reaction Steps

2-Chloro-3-methyl-5-nitropyridine (67.0 g, 0.389 mol) was dissolved in anhydrous methanol (600 ml) and 0.5 M NaOMe in MeOH (800 mL) was added slowly to the mixture (temperature rises to ca. 30° C.). The reaction mixture was stirred at room temperature overnight. The solution was concentrated and the residue was transferred to a separatory funnel containing water (2 L). The aqueous layer was extracted with CH2Cl2 (2×2 L). The combined organic layers were dried over MgSO4, filtered and concentrated to give 2-methoxy-3-methyl-5-nitropyridine (63.0 g, 97% yield) as a white solid which was dried under vacuum: 1H NMR (400 MHz, CDCl3) δ 8.91 (d, J=2.0 Hz, 1H), 8.16 (s, 1H), 4.06 (s, 3H), 2.25 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 165.83, 141.91, 139.37, 132.92, 121.77, 54.83, 15.84; An analytical sample was recrystallized from hexane to give white needles, mp 95-96. 5° C.

Provenance & Evidence