1-Chloroanthraquinone → 1-(1-Ethylpropylamino)anthraquinone

HRID 441106

Reaktionsgleichung

Reaktionsgleichung von HRID 441106
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:18]([CH:20]([NH2:23])[CH2:21][CH3:22])[CH3:19].C([O-])(=O)C.[K+]>[Cu].O>[CH2:18]([CH:20]([NH:23][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:21][CH3:22])[CH3:19]

Komponenten

6

Edukt 3

HCID 67091-ChloroanthraquinoneHCID 120193-PentanamineHCID 517044Potassium Acetate

Produkt 1

HCID 229162751-(1-Ethylpropylamino)anthraquinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A Parr stainless steel high pressure reactor was charged with 1-chloroanthraquinone (24.3 g), 1-ethylpropylamine (17.5 g), potassium acetate (14.0 g), activated copper metal (0.7 g), and water (0.05 g). The reaction vessel was sealed and heated to a temperature of 180° C. in an oil bath and maintained at that temperature for 12 hours. The oil bath was removed and the vessel was allowed to return to ambient conditions. The solid was extracted with methylene chloride and the insoluble materials removed by filtration. The solvent was removed and the solid recrystallized from hot methanol. The material was chromatographed on a silica gel column using toluene as the eluent.

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperaturemaintained at that temperature for 12 hours
  3. customThe oil bath was removed
  4. extractionThe solid was extracted with methylene chloride
  5. customthe insoluble materials removed by filtration
  6. customThe solvent was removed
  7. customthe solid recrystallized from hot methanol
  8. customThe material was chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-4695c54ee1f1423bbc8ddde782de8afb
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521271

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