3-Nitro-pyridine-2,4-dicarboxylic acid diethyl ester → Diethyl 3-aminopyridine-2,4-dicarboxylate

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Reaction Steps

To a solution of 3-Nitro-pyridine-2,4-dicarboxylic acid diethyl ester (55.00 g; 0.19 mol) was added Palladium on carbon (10% w/w) (6.00 g; 0.01 mol). The mixture was stirred at room temperature for 4 hours under 5 Kg of hydrogen pressure. After completion of the reaction, the reaction mixture was filtered through celite and the filtrate concentrated under vacuum. The residue was purified by column chromatography (60-120 mesh) using 15-20% EtOAc: petroleum ether to afford the title compound as a yellow solid (yield 69.7%). LC-MS [239 (M+H)], 1H NMR (400 MHz, DMSO-d6), 7.94-7.93 (d, 1H), 7.84-7.83 (d, 1H), 4.34-4.27 (m, 4H), 1.33-1.29 (m, 6H)

Provenance & Evidence