Ethyl cyanoacetate → 3,5-Bis-ethoxycarbonyl-6-methyl-2-pyridone

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Reaction Steps

Ethylcyanoacetate (2.26 g, 0.02 mol) was added to a NaOEt solution (prepared from 0.46 g of sodium metal in 50 ml EtOH), followed by compound 1 (3.72 g, 0.02 mol). The solution was refluxed for 12 hours. Shiny, light-yellow crystals precipitated out after 18 hours of standing at room temperature. After decolorizing with Nuchar activated carbon, white crystals of 3,5-bis-ethoxycarbonyl-6-methyl-2-pyridone were obtained: 1.45 g, 29% yield; mp=195°-197° C.; NMR (DMSO-d6) δ 1.1-1.5 (t, 6H), 2.6 (s, 3H), 4.1-4.5 (q, 4H), 8.6 (s, 1H), 12.6 (NH); IR (KBr) 1660 cm-1 (C=O of pyridone), 1700 cm-1 and 1720 cm-1 (C=O of ester).

Provenance & Evidence