Hydrochloric Acid → 1-Aminoanthraquinone

HRID 1658863Notes

Reaction equation

HRID 1658863 reaction equation
O[NH:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.C(OCCO)CCC.Cl>[Fe].O>[NH2:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 81332-ButoxyethanolHCID 178514954HCID 178514954, compound

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

50 Parts of 1-hydroxylaminoanthraquinone was stirred into a mixture of 500 parts of ethyleneglycol monobutyl ether, 200 parts of water and 60 parts of a 35 % aqueous hydrochloric acid. After heated to 75°C, the mixture was added with 17 parts of iron ribbon little by little over 1 hour and maintained at 75°C for additional 3 hours. After cooled to 25°C, the reaction mixture was filtered and the residue was washed with water and extracted with 500 parts of dimethylformamide to separate the resulting 1-aminoanthraquinone from unreacted metal. The extract was distilled for removal of dimethylformamide to obtain 42.5 parts of 1-aminoanthraquinone of a purity of 93 %.

Workup

  1. temperaturemaintained at 75°C for additional 3 hours
  2. temperatureAfter cooled to 25°C
  3. filtrationthe reaction mixture was filtered
  4. washthe residue was washed with water
  5. extractionextracted with 500 parts of dimethylformamide
  6. customto separate the resulting 1-aminoanthraquinone from unreacted metal
  7. distillationThe extract was distilled for removal of dimethylformamide

Sources & evidence

ORD record
ord-d3b7105e718f44579b54a4cf5421cc4f
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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