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

HRID 260817

Reaction equation

HRID 260817 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.[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]

Participants

6

Reactant 3

HCID 67091-ChloroanthraquinoneHCID 120193-PentanamineHCID 517044Potassium Acetate

Product 1

HCID 229162751-(1-Ethylpropylamino)anthraquinone

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

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 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.

Workup

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

Sources & evidence

ORD record
ord-900e32d5cc3c440e9f39f7144b589599
Source dataset
uspto-grants-1996_06
Patent number
US05530067

Linked notes

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