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

HRID 260814

Reaction equation

HRID 260814 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

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 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.

Workup

  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 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

Sources & evidence

ORD record
ord-6ac2a04d0b45468380ff61645b55b12c
Source dataset
uspto-grants-1996_06
Patent number
US05530053

Linked notes

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