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

HRID 1729568Notes

Reaction equation

HRID 1729568 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.-butylaniline are stirred at 125° C until no further dinitro-anthraquinone 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-9de4435a2650493ea834b75ac03efc9b
Source dataset
uspto-grants-1976_11
Patent number
US03989450

Reaction notes

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