Ammonia → HCID 13654876, Verbindung

HRID 1199401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199401
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH:7]=[CH:8][C:9](=O)[CH2:10]C(OCC)=O)([O-:3])=[O:2].O=[C:21]([CH2:28][O:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[NH3:36]>C(O)C>[CH2:26]([O:25][C:23]([C:8]1[CH:7]([C:6]2[CH:17]=[CH:18][CH:19]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:21]([CH2:28][O:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[NH:36][C:9]=1[CH2:10][O:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:24])[CH3:27]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 21253101Ethyl 3-oxo-4-[(pyridin-3-yl)oxy]butanoateHCID 53828414HCID 53828414, Verbindung

Produkt 1

HCID 13654876HCID 13654876, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between 2N hydrochloric acid and diethyl ether
  3. extractionThe aqueous acid was extracted with chloroform
  4. washthis was washed with dilute ammonia solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by chromatography on silica with first chloroform

Quellen und Nachweise

ORD-Eintrag
ord-2a6a250c2c2646d4ac6f09cad2a0853c
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900750

Notizen zur Reaktion

Wird geladen…