3-Nitrobenzaldehyde → 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine

Participants

Reaction Steps

A mixture of 4.3 g of 2-(4-hydroxyphenyl)ethylacetoacetate (10), 2.3 g of methyl β-amino-crotonate, 2.9 g of 3-nitrobenzaldehyde and 70 mL of methanol was heated at reflux for 12 hours. The solvent was removed under reduced pressure and the residue purified by silica gel chromatography using 50:50 ethyl acetate-hexane to yield 5.9 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine (11), as an amorphous solid.

Provenance & Evidence