Diphenyl Ether → HCID 21250045, Verbindung

HRID 1531695

Reaktionsgleichung

Reaktionsgleichung von HRID 1531695
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]2[Cl:17].C([O:20][CH:21]=[C:22]([C:28]([CH3:30])=[O:29])[C:23](OCC)=O)C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:28]([CH:22]1[C:21](=[O:20])[C:3]2[C:2](=[C:11]3[C:6](=[CH:5][CH:4]=2)[C:7]([Cl:17])=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[N:10]3)[N:1]=[CH:23]1)(=[O:29])[CH3:30]

Komponenten

5

Edukt 3

HCID 7583Diphenyl EtherHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl esterHCID 21250075HCID 21250075, Verbindung

Produkt 1

HCID 21250045HCID 21250045, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 8-amino-4-chloro-3-ethoxycarbonylquinoline (0.3 g) and ethyl 2-ethoxymethyleneacetoacetate (Annalen, 1897, 297, 16, 0.25 g) was heated at 90° C. for 2.5 hours. The mixture was cooled to ambient temperature and the resulting solid added to diphenyl ether at reflux. The mixture was refluxed for 45 minutes, and cooled to 60° C. The mixture was diluted with carbon tetrachloride (50 ml) and cooled to ambient temperature with stirring. The mixture was filtered and the solid so obtained purified by flash chromatography on silica using increasingly polar mixtures of methanol and chloroform. The product so obtained was recrystallised from methanol to give 3-acetyl-7-chloro-8-ethoxycarbonyl-4-oxo-3,4-dihydro-1,10-phenanthroline in 29% yield, mp 288-290° C.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperatureat reflux
  3. temperatureThe mixture was refluxed for 45 minutes
  4. temperaturecooled to 60° C
  5. temperaturecooled to ambient temperature
  6. filtrationThe mixture was filtered
  7. customthe solid so obtained
  8. custompurified by flash chromatography on silica using
  9. temperatureincreasingly polar mixtures of methanol and chloroform
  10. customThe product so obtained
  11. customwas recrystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-fc9b0aec85c8416fb9bf4fc9609b7222
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06200974B1

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