3-Nitrobenzaldehyde → beta-n-Propoxyethyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(3-nitrophenyl)-pyridine-5-carboxylate

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Reaction Steps

15.1 g (0.1 mol) of 3-nitrobenzaldehyde, together with 18.8 g (0.1 mol) of β-n-propoxyethyl acetoacetate and 10.2 g (0.1 mol) of 2-amino-1-nitro-prop-1-ene in 150 ml of ethanol, were heated uder reflux for 6 hours. After cooling, the solvent was distilled off in vacuo, and the oily residue was taken up in a small amount of chloroform and was chromatographed on a silica gel column, using chloroform with the addition of methanol. The fractions containing the product were concentrated, the residue was taken up in a small amount of isopropanol, and the nitrodihydropyridine crystallized in yellow crystals of melting point 161° C.

Provenance & Evidence