2-Methoxyaniline → 1-o-Anisidino-7-nitro-anthraquinone

HRID 2418995Notes

Reaction equation

HRID 2418995 reaction equation
[N+]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N+:19]([O-:21])=[O:20])[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[C:26]([NH2:31])=[CH:27][CH:28]=[CH:29][CH:30]=1>COCCO>[CH3:23][O:24][C:25]1[C:26]([NH:31][C:4]2[C:17]3[C:16](=[O:18])[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=4)[C:9](=[O:22])[C:8]=3[CH:7]=[CH:6][CH:5]=2)=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 741471,7-Dinitroanthraquinone

Product 1

HCID 203164851-o-Anisidino-7-nitro-anthraquinone

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

50 g of 1,7-dinitro-anthraquinone and 150 ml of o-anisidine are stirred for 9 hours at 120° - 125° C and then diluted with 150 ml of ethylene glycol monomethyl ether, the mixture is stirred until cold and stirred for several hours longer in an ice bath, and the product is filtered off and successively washed with a little ethylene glycol monomethyl ether, methanol and water. 40.4 g of 1-o-anisidino-7-nitro-anthraquinone are obtained.

Workup

  1. stirringstirred for several hours longer in an ice bath
  2. filtrationthe product is filtered off
  3. washsuccessively washed with a little ethylene glycol monomethyl ether, methanol and water

Sources & evidence

ORD record
ord-57725fdada4c401e999fc4d4b82f025d
Source dataset
uspto-grants-1978_08
Patent number
US04104284

Reaction notes

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