Hydrochloric Acid → 1-Aminoanthraquinone

HRID 1658859Notes

Reaction equation

HRID 1658859 reaction equation
CO.Cl.O[NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1>[Fe].O>[NH2:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178514954HCID 178514954, compound

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 600 parts of methyl alcohol, 200 parts of water and 70 parts of a 35% aqueous hydrochloric acid there was added with stirring 50 parts of 1-hydroxylaminoanthraquinone and the resulting mixture was heated to 70°C. After addition of 17 parts of metallic iron in the form of ribbon little by little over 1 hour, the reaction mixture was maintained at 70°C for additional 4 hours, then cooled to 25°C and filtered. The residue was washed with water, then dissolved in 500 parts of dimethylformamide and filtered to remove residual metallic iron. Dimethylformamide in the filtrate was removed by distillation under reduced pressure to obtain 42.0 parts of 1-aminoanthraquinone of a purity of 92%.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was maintained at 70°C for additional 4 hours
  3. temperaturecooled to 25°C
  4. filtrationfiltered
  5. washThe residue was washed with water
  6. dissolutiondissolved in 500 parts of dimethylformamide
  7. filtrationfiltered
  8. customto remove residual metallic iron
  9. customDimethylformamide in the filtrate was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5629744c307d4e80813f5da48f9697ba
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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