P-Anisidine → 1-p-Anisidino-6-nitro-anthraquinone

HRID 1729569

Reaction equation

HRID 1729569 reaction equation
[N+]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[CH:13][CH:14]=3)[C:9](=[O:22])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:4]2[C:17]3[C:16](=[O:18])[C:15]4[C:10](=[CH:11][C:12]([N+:19]([O-:21])=[O:20])=[CH:13][CH:14]=4)[C:9](=[O:22])[C:8]=3[CH:7]=[CH:6][CH:5]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 741461,6-Dinitroanthraquinone

Product 1

HCID 203164871-p-Anisidino-6-nitro-anthraquinoneYield 99.6%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

100 g of 1,6-dinitro-anthraquinone and 84 g of p-anisidine are stirred in 300 ml of nitrobenzene at 150° C until no further starting material is detectable in a sample. The mixture is now distilled to dryness in a Venuleth apparatus under a vacuum of 5 mm and the finely ground residue is thoroughly stirred with dilute sulphuric acid, filtered off, washed until neutral and dried. 125 g of 1-p-anisidino-6-nitro-anthraquinone are obtained.

Workup

  1. distillationThe mixture is now distilled to dryness in a Venuleth apparatus under a vacuum of 5 mm
  2. filtrationfiltered off
  3. washwashed until neutral and
  4. customdried

Sources & evidence

ORD record
ord-774bab5d46c545caa587534f7bde833c
Source dataset
uspto-grants-1976_11
Patent number
US03989450

Linked notes

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