9,10-Anthracenedione, 1,2-dinitro- → 1-(p-Tert.-butyl-anilino)-6-nitro-anthraquinone

HRID 2418993

Reaction equation

HRID 2418993 reaction equation
[N+:1]([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.[C:23]([C:27]1[CH:33]=[CH:32][C:30](N)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].[N+](C1C=CC2C(=O)C3C(=CC=CC=3)C(=O)C=2C=1[N+]([O-])=O)([O-])=O>COCCO>[C:23]([C:27]1[CH:33]=[CH:32][C:30]([NH:1][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:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 425969,10-Anthracenedione, 1,2-dinitro-HCID 698614-Tert-ButylanilineHCID 741461,6-Dinitroanthraquinone

Product 1

HCID 203164881-(p-Tert.-butyl-anilino)-6-nitro-anthraquinone

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

The product employed in a) can be obtained as follows: 15 g of 1,6-dinitro-anthraquinone and 30 ml of p-tert.-butyl-aniline are stirred at 125° C until no further dinitroanthraquinone is detectable (approx. 6 hours being required). The warm mixture is diluted with 30 ml of ethylene glycol monomethyl ether, stirred until cold and filtered, and the residue is successively washed with ethylene glycol monomethyl ether and water. 13.9 g of 1-(p-tert.-butyl-anilino)-6-nitro-anthraquinone are obtained.

Workup

  1. customcan be obtained
  2. custom(approx. 6 hours being required)
  3. filtrationfiltered
  4. washthe residue is successively washed with ethylene glycol monomethyl ether and water

Sources & evidence

ORD record
ord-f04b534a85eb4b7a8780828f9963aac0
Source dataset
uspto-grants-1978_08
Patent number
US04104284

Linked notes

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