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

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Reaction Steps

A mixture of 4.3 g of 2-(4-hydroxyphenyl)-ethylacetoacetate (10), 2.3 g of methyl β-aminocrotonate, 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. Calculated for C24H24N2O7.1.5H2O: C-60.12, H-5.68, N-5.84. Found: C-60.55, H-5.33, N-6.03.

Provenance & Evidence