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

HRID 1389040

Reaction equation

HRID 1389040 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.CO>[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 887MethanolSolventHCID 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 methanol 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 7.6 parts of 1,4-diaminoanthraquinone-2-carboxylic acid.

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-46ce56ccbc324e859200914367a25e04
Source dataset
uspto-grants-1981_01
Patent number
US04243600

Linked notes

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