1-Chloroanthraquinone → 1-[4-[2-Hydroxyethyl]phenyl]aminoanthraquinone

HRID 1376306

Reaktionsgleichung

Reaktionsgleichung von HRID 1376306
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.[NH2:18][C:19]1[CH:27]=[CH:26][C:22]([CH2:23][CH2:24][OH:25])=[CH:21][CH:20]=1.C([O-])(=O)C.[K+].[N+](C1C=CC=CC=1)([O-])=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[OH:25][CH2:24][CH2:23][C:22]1[CH:26]=[CH:27][C:19]([NH:18][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7](=[O:17])[C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 67091-ChloroanthraquinoneHCID 7416NitrobenzeneHCID 669044-Aminophenethyl alcoholHCID 517044Potassium Acetate

Produkt 1

HCID 99280421-[4-[2-Hydroxyethyl]phenyl]aminoanthraquinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8895Cupric acetateKatalysator

Versuchsvorschrift

HEPAAQ was prepared by a procedure described in Lord, M. W.; Peters, A. T.; J. Chem. Soc., Perkins Trans., 1,(20)2305-8, incorporated herein by reference, with a slight modification. In a 250 mL single-necked round-bottom flask equipped with a reflux condenser was placed 1-chloroanthraquinone (10.5 g), 4-aminophenethyl alcohol (11.2 g), potassium acetate (7.87 g), copper acetate (0.46 g), and nitrobenzene (75 mL). The flask was flushed with nitrogen and then heated to reflux for about 2 hours. The resulting mixture was filtered. The solvent was removed from the filtrate, and the resultant solid was washed with methanol. The product was purified by dissolving the dried filtrate in dichloromethane and chromatographing on a silica column using a 10/90 (v/v) acetone/dichloromethane mixture as the eluent. The solvent was removed from the chromatographed material and dried in vacuo.

Aufarbeitung

  1. customHEPAAQ was prepared by a procedure
  2. customIn a 250 mL single-necked round-bottom flask equipped with a reflux condenser
  3. customThe flask was flushed with nitrogen
  4. temperatureheated
  5. temperatureto reflux for about 2 hours
  6. filtrationThe resulting mixture was filtered
  7. customThe solvent was removed from the filtrate
  8. washthe resultant solid was washed with methanol
  9. customThe product was purified
  10. dissolutionby dissolving the dried filtrate in dichloromethane
  11. customThe solvent was removed from the chromatographed material
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a6c7097116574a729bb00fdf365e2316
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663024

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