Hydrochloric Acid → 1-Amino-6,7-dimethylanthracene-9,10-dione

HRID 1658865Notes

Reaction equation

HRID 1658865 reaction equation
[CH3:1][C:2]1[C:15]([CH3:16])=[CH:14][C:13]2[C:12](=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[NH:18]O)[C:5](=[O:20])[C:4]=2[CH:3]=1.CO.COCCO.Cl>[Zn].O>[CH3:1][C:2]1[C:15]([CH3:16])=[CH:14][C:13]2[C:12](=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[NH2:18])[C:5](=[O:20])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 80192-MethoxyethanolHCID 178421830HCID 178421830, compound

Product 1

HCID 212925531-Amino-6,7-dimethylanthracene-9,10-dione

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

50 Parts of 2,3-dimethyl-5-hydroxylaminoanthraquinone was stirred into a mixture of 700 parts of ethyleneglycol monomethyl ether, 200 parts of water and 60 parts of a 35 % aqueous hydrochloric acid, and the mixture was then heated to 75°C. To the mixture there was added little by little 16 parts of zinc dust over 1 hour. The reaction mixture was maintained at 75°C for additional 3 hours, then cooled to 25°C and filtered. The residue was washed with water and dried to obtain 43.6 parts of 2,3-dimethyl-5-aminoanthraquinone of a purity of 95 %.

Workup

  1. temperatureThe reaction mixture was maintained at 75°C for additional 3 hours
  2. temperaturecooled to 25°C
  3. filtrationfiltered
  4. washThe residue was washed with water
  5. customdried

Sources & evidence

ORD record
ord-70aece485f4f4adea7fb7a4b81ebc599
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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