Phenol → 9,10-Anthracenedione, 1-amino-4,5-dihydroxy-8-nitro-

HRID 2071670

Reaction equation

HRID 2071670 reaction equation
[N+](C1C2C(=O)C3C(=C([N+]([O-])=O)C=CC=3O)C(=O)C=2C(O)=CC=1)([O-])=O.[N+:25]([C:28]1[C:41]2[C:40](=[O:42])[C:39]3[C:34](=[C:35]([OH:46])[CH:36]=[CH:37][C:38]=3[N+:43]([O-])=O)[C:33](=[O:47])[C:32]=2[C:31]([OH:48])=[CH:30][CH:29]=1)([O-:27])=[O:26].C1(O)C=CC=CC=1>CO>[NH2:43][C:38]1[C:39]2[C:40](=[O:42])[C:41]3[C:32](=[C:31]([OH:48])[CH:30]=[CH:29][C:28]=3[N+:25]([O-:27])=[O:26])[C:33](=[O:47])[C:34]=2[C:35]([OH:46])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 30909169,10-Anthracenedione, 1,5-dihydroxy-4,8-dinitro-HCID 33784401,8-Dinitro-4,5-dihydroxyanthraquinone

Product 1

HCID 54840799,10-Anthracenedione, 1-amino-4,5-dihydroxy-8-nitro-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.5 parts of a mixture of 1,5-dinitro-4,8-dihydroxyanthraquinone and 1,8-dinitro-4,5-dihydroxyanthraquinone (about 1:1 parts) is heated with 50 parts of phenol for eight hours at 180° C while stirring. After cooling 100 parts by volume of methanol is added, the precipitate is suction filtered and the residue is washed with methanol and then with hot water. After drying 13 parts of a mixture of 1-amino-5-nitro-4,8-dihydroxyanthraquinone and 1-amino-8-nitro-4,5-dihydroxyanthraquinone is obtained; this is equivalent to 87% of the calculated yield.

Workup

  1. additionis added
  2. filtrationfiltered
  3. washthe residue is washed with methanol
  4. customAfter drying
  5. addition13 parts of a mixture of 1-amino-5-nitro-4,8-dihydroxyanthraquinone

Sources & evidence

ORD record
ord-e7ce05f0396f4909a73243b9ac0db4b4
Source dataset
uspto-grants-1977_09
Patent number
US04048199

Linked notes

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