Hydrochloric Acid → 1,4-Diamino-9,10-dioxoanthracene-2-carboxylic acid

HRID 1389039

Reaction equation

HRID 1389039 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][C:5]=1[C:20]([OH:22])=[O:21])([O-])=O.Cl.[NH2:24]O.[OH-].[Na+].Cl>O.C(O)C>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[C:7]([NH2:24])=[CH:6][C:5]=1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 314131-Nitroanthraquinone-2-carboxylic acidHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 33587451,4-Diamino-9,10-dioxoanthracene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10 parts of 1-nitroanthraquinone-2-carboxylic acid and 10 parts of hydroxylamine hydrochloride are suspended at room temperature in 60 parts of ethanol and 100 parts of 4 N sodium hydroxide. The mixture is refluxed for 3 hours, then cooled to room temperature, diluted with water and acidified with hydrochloric acid. The mixture is filtered and the filter cake is washed neutral with water and dried, affording 7.5 parts of 1,4-diaminoanthraquinone-2-carboxylic acid. Recrystallisation from alcohol yields an analytically pure sample with a melting point of about 352° C.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. filtrationThe mixture is filtered
  3. washthe filter cake is washed neutral with water
  4. customdried

Sources & evidence

ORD record
ord-2ee09c13697245a8bd3695fe348f2e32
Source dataset
uspto-grants-1981_01
Patent number
US04243600

Linked notes

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