Reaktion #815505

Reaktionsgleichung

2-nicotinoylaminoethyl acetoacetate

m-nitrobenzaldehyde

2-cyanoethyl 3-aminocrotonate

→

2,6-dimethyl4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nicotinoylaminoethyl) ester

Ausbeute 97.1%

Lösungsmittel

isopropyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 5 hours
2. 2
   SonstigeAfter evaporation of the solvent
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 200 ml of acetone
4. 4
   workup.ADDITIONTo the solution was added 200 ml of 0.75 N aqueous sodium hydroxide solution
5. 5
   workup.ADDITION1N hydrochloric acid was added
6. 6
   Einengenthe solution was concentrated
7. 7
   Extraktionextracted with chloroform Evaporation of the solvent

Vorschrift

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.

Quelle