3-Nitrobenzaldehyde → 2,6-Dimethyl4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nicotinoylaminoethyl) ester

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Reaction Steps

To a solution of 25.03 g (100 mole) of 2-nicotinoylaminoethyl acetoacetate, 15.11 g (100 mmole) of m-nitrobenzaldehyde and 15.42 g (100 mmole) of 2-cyanoethyl 3-aminocrotonate in 150 ml of isopropyl alcohol was added 0.73 g (5 mmole) of piperidinium acetate, and the mixture was refluxed for 5 hours. After evaporation of the solvent, the residue was dissolved in 200 ml of acetone. To the solution was added 200 ml of 0.75 N aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for an hour. 1N hydrochloric acid was added, and the solution was concentrated and extracted with chloroform Evaporation of the solvent gave 45.27 g of 2,6-dimethyl4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nicotinoylaminoethyl) ester.

Provenance & Evidence