Reaktion #1286583

Reaktionsgleichung

Ethyl 3-nitrobenzylideneacetoacetate

ethyl 3-oxo-4-(3-pyridyloxy)butanoate

ammonia

→

title compound

1,4-Dihydro-2,6-di[(3-pyridyloxy)-methyl]-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid diethyl ester

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   Sonstigethe residue partitioned between 2N hydrochloric acid and diethyl ether
3. 3
   ExtraktionThe aqueous acid was extracted with chloroform
4. 4
   Waschenthis was washed with dilute ammonia solution
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by chromatography on silica with first chloroform

Vorschrift

Ethyl 3-nitrobenzylideneacetoacetate (6.47 g. 0.026 mol), ethyl 3-oxo-4-(3-pyridyloxy)butanoate (5.8 g, 0.026 mol) and 0.88 ammonia (2.5 ml) in ethanol were refluxed for 7 hours. The solvent was removed under reduced pressure and the residue partitioned between 2N hydrochloric acid and diethyl ether. The aqueous acid was extracted with chloroform and this was washed with dilute ammonia solution, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica with first chloroform then ethyl acetate as eluent to obtain the title compound. This was dissolved in ethanol and acidified with ethanolic HCl to give the dihydrochloride salt of the title compound (0.95 g) m.p. 206-208° C.

Quelle