Reaktion #629414

ord-55e9bc710fbd47f0a4bd2b97c284c7eb

Reaktionsgleichung

CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1
2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate
CCOC(=O)/C=C(/C)N
ethyl 3-aminocrotonate
CCO
ethanol
→
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOc2ccc(NC(C)=O)cc2)C1c1cccc([N+](=O)[O-])c1
2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4dihydropyridine-3-carboxylate
Ausbeute 75.0%

Edukte

CC(=O)Nc1ccc(OCCOC(=O)CC(=O)C=Cc2cccc([N+](=O)[O-])c2)cc1
2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate
CCOC(=O)/C=C(/C)N
ethyl 3-aminocrotonate
CCO
ethanol

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
-5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

12.28 g (0.03 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 3.85 g (0.03 moles) of ethyl 3-aminocrotonate are heated under reflux in 30 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in ethanol--at 198°-200° C. The yield is 75% of the theoretical yield.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04656181uspto-grants-1987_04