9,10-Anthracenedione, 1-bromo-4-(methylamino)- → 1-Methylamino-4-(p-trifluoromethoxy-anilino)-anthraquinone

HRID 258987

Reaction equation

HRID 258987 reaction equation
[CH3:1][NH:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[C:6](Br)=[CH:5][CH:4]=1.[F:20][C:21]([F:31])([F:30])[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.C([O-])(=O)C.[K+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][NH:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[C:6]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([O:22][C:21]([F:20])([F:30])[F:31])=[CH:24][CH:25]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 314189,10-Anthracenedione, 1-bromo-4-(methylamino)-HCID 517044Potassium AcetateHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 214250741-Methylamino-4-(p-trifluoromethoxy-anilino)-anthraquinone

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Conditions

Temperature
132 °C

Procedure

12.64 parts of 1-methylamino-4bromo-anthraquinone, 9.9 parts of para-trifluoromethoxyaniline, 6 parts of potassium acetate and 2 parts of copper acetate are introduced into 43 parts of 4-methyl-2-pertanol and the mixture is heated at 132° C. for 8 hours. The mixture is then cooled to 60° C., filtered, washed with water, then the precipitate is taken up in dilute caustic soda, filtered, washed and dried. 9.6 parts of 1-methylamino-4-(p-trifluoromethoxy-anilino)-anthraquinone are obtained.

Workup

  1. temperatureThe mixture is then cooled to 60° C.
  2. filtrationfiltered
  3. washwashed with water
  4. filtrationfiltered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-ac64c7d594e14581bcbb8eb574d9b28c
Source dataset
uspto-grants-1977_07
Patent number
US04035397

Linked notes

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