Acetoacetic Acid → 5-Methoxycarbonyl-6-dimethoxymethyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Participants

Reaction Steps

A solution of 3-nitrobenzaldehyde (3.02 g), 3-nitrooxy-2,2-bis(nitrooxymethyl)propyl ester of acetoacetic acid (7.10 g) and methyl 3-amino-4,4-dimethoxycrotonate (3.50 g) dissolved in tert-butyl alcohol (12 ml) was refluxed for 15 hours. The resulting mixture was cooled and concentrated under reduced pressure. The residue obtained was subjected to column chromatography on silica gel (200 g) and eluted with a mixture of toluene and ethyl acetate (10:1 by volume). The fractions containing the desired compound were collected and evaporated under reduced pressure to give a viscous oil of 3-nitrooxy-2,2-bis(nitrooxymethyl)propyl ester of 5-methoxycarbonyl-6-dimethoxymethyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (8.60 g).

Provenance & Evidence