p-Toluidine → 1-(Methylamino)-4-((4-methylphenyl)amino)anthraquinone

HRID 1199755Notes

Reaction equation

HRID 1199755 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][NH:10][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14](Br)=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>CO.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:9][NH:10][C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[C:14]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7813p-ToluidineHCID 314189,10-Anthracenedione, 1-bromo-4-(methylamino)-HCID 517045Sodium Acetate

Product 1

HCID 671951-(Methylamino)-4-((4-methylphenyl)amino)anthraquinoneYield 82%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent

Procedure

In a reactor were charged p-toluidine (80 parts), 1-methylamino-4-bromoanthraquinone (15.8 parts), sodium acetate (7.5 parts) and copper acetate (0.5 part) and the mixture was kept at 115° to 120° C. for 6 hours under a nitrogen atmosphere. Thereafter, the reaction mixture was diluted with methanol (100 parts) and cooled. The precipitate produced was filtrated, washed with methanol (500 parts) and then water (200 parts), and dried at 80° to 90° C. to obtain 1-methylamino-4-(4'-methylanilino)-anthraquinone (yield 82%).

Workup

  1. temperaturecooled
  2. customThe precipitate produced
  3. filtrationwas filtrated
  4. washwashed with methanol (500 parts)
  5. dry with materialwater (200 parts), and dried at 80° to 90° C.

Sources & evidence

ORD record
ord-898959b639a845fca73b13ecc9ee2bad
Source dataset
uspto-grants-1990_02
Patent number
US04902798

Reaction notes

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