Hydrochloric Acid → 1-Aminoanthraquinone

HRID 1658861Notes

Reaction equation

HRID 1658861 reaction equation
Cl.O[NH:3][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][CH:5]=1>[Zn]>[NH2:3][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][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178514954HCID 178514954, compound

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
70 °C

Procedure

To 700 parts of a 3 % aqueous hydrochloric acid there was added 50 parts of 1-hydroxylaminoanthraquinone and the mixture was heated with stirring to 70°C, then added thereto little by little 16 parts of zinc dust over 1 hour. The reaction mixture was maintained at 70°C for additional 4 hours. Zinc dust was completely consumed during the reaction course but a fairly large amount of 1-hydroxylaminoanthraquinone remained unreacted. The reaction mixture was cooled to 25°C and filtered. The residue was washed with water and then with 200 parts of a 3 % solution of sodium hydroxide in a 20 % aqueous acetone to extract therefrom unreacted 1-hydroxylaminoanthraquinone and washed with water again and dried to obtain 15.5 parts of 1-aminoanthraquinone of a purity of 90 %.

Workup

  1. temperaturethe mixture was heated
  2. additionadded
  3. temperatureThe reaction mixture was maintained at 70°C for additional 4 hours
  4. customZinc dust was completely consumed during the reaction course
  5. temperatureThe reaction mixture was cooled to 25°C
  6. filtrationfiltered
  7. washThe residue was washed with water
  8. extractionwith 200 parts of a 3 % solution of sodium hydroxide in a 20 % aqueous acetone to extract
  9. washunreacted 1-hydroxylaminoanthraquinone and washed with water again
  10. customdried

Sources & evidence

ORD record
ord-26fda22513bf4c07ba34fc04bd732509
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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