Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate → 5-Bromo-2-methyl-3-nitropyridine

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Reaction Steps

A stirred mixture of diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (12.5 g, 34.6 mmol) in HCl (7 N in water, 200 mL) is heated at reflux for 18 hours. The mixture is cooled to room temperature and extracted with CH2Cl2 (3×200 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via chromatography using CH2Cl2 to afford the title compound (5.8 g, 84%) as a yellow solid: Rf 0.67 (CH2Cl2); LCMS (m/z)=217.1, 219.2 [M+H]+, tR=2.01 min.

Provenance & Evidence