1-Nitroanthraquinone → 9,10-Anthracenedione, 1-(cyclohexylamino)-

HRID 261007

Reaction equation

HRID 261007 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[CH:20]1(N)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>CC1C=CC(C(C)C)=CC=1>[CH:20]1([NH:1][C:4]2[C:17]3[C:16](=[O:18])[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9](=[O:19])[C:8]=3[CH:7]=[CH:6][CH:5]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 67041-NitroanthraquinoneHCID 7965Cyclohexylamine

Product 1

HCID 706699,10-Anthracenedione, 1-(cyclohexylamino)-Yield 94%

Reagents, catalysts & solvents 1

HCID 7463P-CymeneSolvent

Procedure

25.3 g of 1-nitroanthraquinone (99% pure) in 120 ml of p-cymene are boiled together with 29.8 g of cyclohexylamine (molar ratio 3:1) for 2 hours under reflux. After cooling the reaction mixture, 150 ml of petroleum ether are added, the mixture is filtered and the residue is washed with petroleum ether and dried. 28.1 g (94% of theory) of cyclohexylamino-anthraquinone are obtained. No further starting material can be detected by means of thin layer chromatography.

Workup

  1. temperatureunder reflux
  2. additionare added
  3. filtrationthe mixture is filtered
  4. washthe residue is washed with petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-ff7db9d3e9404a2caf01d3b13cb2559f
Source dataset
uspto-grants-1979_08
Patent number
US04163747

Linked notes

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