Ethanol → 2-Ethoxy-5-nitropyridine

関与物質

反応手順

To anhydrous ethanol (250 ml) were added sodium (2.25 g, 97.8 mmol) then 2-chloro-5-nitropyridine (15 g, 9.46 mmol) under argon. The resulting mixture was heated at reflux for 10 hrs. After cooling slightly, the mixture was filtered to remove undissolved particles. The filtrate was condensed by rotary evaporation. The residue was triturated with abs ethanol (50 ml). The solid was collected by filtration and dried giving 13.5 g of the product: mp 90-92° C. mass spectrum (electrospray, m/e): 169 (M+H); IR cm-1: 1600, 1508, 1378, 1290, 1118, 1027; H-NMR δ (CDCl3) 1.431 (3H, t, CH3), 4.512 (2H, q, CH2), 6.800 (1H, d, C3-H), 8.337 (1H, dd, C4-H), 9.068 (1H, d, C5-H). See: Friedman et. al., J. Amer. Che. Soc., 69, 1947, 1204.

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