Dimethyl 2-(3-nitropyridin-2-yl)malonate → 2-Methyl-3-nitropyridine

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Reaction Steps

A modified procedure of Cash et al. (Org. Biomol. Chem. 2005, 3. 3701-3706) was used. Dimethyl-2-(3-nitropyridin-2-yl)malonate (1.4 g, 5.5 mmol) was dissolved in 70 ml 6 M HCl and refluxed for 8 h. After neutralization with saturated Na2CO3 solution the solution was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by bulb tube distillation (0.35 mbar; 70-80° C.). 2-Methyl-3-nitropyridine (0.7 g, 5.1 mmol, 92%) was obtained as a pale yellow oil. 1H NMR (300 MHz, CDCl3) 8.72 (pdd; 3J=1.2 Hz; 3J=4.7 Hz; 1H; H-6); 8.27 (pdd; 3J=1.2 Hz; 3J=8.2 Hz; 1H; H-4); 7.35 (pdd; 3J=4.7 Hz; 3J=8.2 Hz; 1H; H-5); 2.86 (s; 3H; CH3).

Provenance & Evidence