1,5-Dichloroanthraquinone → 1,5-Bis(4-cyclohexylphenylamino)-anthraquinone

HRID 256276Notes

Reaction equation

HRID 256276 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:19]1([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[C:32]([O-])(=O)[CH3:33].[Na+].[N+:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([O-])=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CO>[CH:19]1([C:25]2[CH:26]=[CH:27][C:28]([NH:29][C:2]3[C:15]4[C:14](=[O:16])[C:13]5[C:8](=[C:9]([NH:37][C:40]6[CH:45]=[CH:44][C:43]([CH:32]7[CH2:33][CH2:4][CH2:3][CH2:2][CH2:15]7)=[CH:42][CH:41]=6)[CH:10]=[CH:11][CH:12]=5)[C:7](=[O:18])[C:6]=4[CH:5]=[CH:4][CH:3]=3)=[CH:30][CH:31]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

7

Reactant 4

HCID 67111,5-DichloroanthraquinoneHCID 7416NitrobenzeneHCID 807644-CyclohexylbenzenamineHCID 517045Sodium Acetate

Product 1

HCID 201633301,5-Bis(4-cyclohexylphenylamino)-anthraquinone

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent

Procedure

In a round bottom flask equipped with stirrer, thermometer, and nitrogen inlet is added 2.77 g (0.1M) 1,5-bischloroanthraquinone and 3.5 g (0.2M) of 4-cyclohexylaniline. 3.0 g anhydrous sodium acetate and 0.1 g anhydrous copper acetate are added as acid acceptor and reaction catalyst respectively. 50 g nitrobenzene are added and the stirred mass is heated to reflux under nitrogen atmosphere. The reaction is allowed to proceed for two hours at 185° C. Upon cooling, 50 g methanol is added and the crude dye separated by vacuum filtration. Subsequent purification by recrystalization and chromatography from alumina using toluene as the elvent affords the magneta pleochroic dye 1,5-bis(4-cyclohexylphenylamino)-anthraquinone. The optical order parameter was measured as 0.7.

Workup

  1. customIn a round bottom flask equipped with stirrer
  2. customacceptor and reaction catalyst respectively
  3. temperaturethe stirred mass is heated
  4. temperatureto reflux under nitrogen atmosphere
  5. temperatureUpon cooling
  6. customthe crude dye separated by vacuum filtration
  7. customSubsequent purification
  8. customby recrystalization and chromatography from alumina

Sources & evidence

ORD record
ord-8d56c5b5a35a4fcda4c347d4ddb3d7c7
Source dataset
uspto-grants-1987_10
Patent number
US04702561

Reaction notes

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