Sulfuric Acid → 1-Aminoanthraquinone

HRID 1658864Notes

Reaction equation

HRID 1658864 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.S(=O)(=O)(O)O>[Fe].COCCO>[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

5

Reactant 2

HCID 1118Sulfuric AcidHCID 178514954HCID 178514954, compound

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
75 °C

Procedure

50 Parts of 1-hydroxylaminoanthraquinone was stirred into a mixture of 1,000 parts of ethyleneglycol monomethyl ether and 30 parts of conc. sulfuric acid. After heated to 75°C, the mixture was added with 17 parts of iron dust little by little over 1 hour and maintained at 75°C for additional 3 hours. The reaction mixture was then filtered while hot and the residue was washed with 100 parts of ethyleneglycol monomethyl ether heated at 80°C. Thus, unreacted metallic iron and iron sulfate were separated as residue. The filtrate was added with 200 parts of water and then cooled to 25°C to precipitate crystals. The crystals were recovered by filtration, washed with water and dried to obtain 43.5 parts of 1-aminoanthraquinone of a purity of 95 %.

Workup

  1. temperaturemaintained at 75°C for additional 3 hours
  2. filtrationThe reaction mixture was then filtered while hot and the residue
  3. washwas washed with 100 parts of ethyleneglycol monomethyl ether
  4. temperatureheated at 80°C
  5. customThus, unreacted metallic iron and iron sulfate were separated as residue
  6. additionThe filtrate was added with 200 parts of water
  7. temperaturecooled to 25°C
  8. customto precipitate crystals
  9. filtrationThe crystals were recovered by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-10f344e577414964976108cbfb3156ba
Source dataset
uspto-grants-1976_06
Patent number
US03966775

Reaction notes

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