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

Participants

Reaction Steps

15.1 g (0.1 mol) of 3-nitrobenzaldehyde, together with 16.9 g (0.1 mol) of cyclopentyl β-aminocrotonate and 10.3 g (0.1 mol) of nitroacetone in 150 ml of ethanol, were heated under reflux for 6 hours. After the reaction mixture had cooled, 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 reaction product were concentrated, the residue was taken up in a small amount of isopropanol, and the nitrodihydropyridine crystallized in yellow crystals of melting point 174° C.

Provenance & Evidence