Hydroquinone → 1-Aminoanthraquinone

HRID 972999

Reaction equation

HRID 972999 reaction equation
[N+:1]([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)([O-])=O.[N+](C1C2C(=O)C3C(=C([N+]([O-])=O)C=CC=3)C(=O)C=2C=CC=1)([O-])=O.[N+](C1C2C(=O)C3C(=CC=CC=3[N+]([O-])=O)C(=O)C=2C=CC=1)([O-])=O.[OH-].[Na+].[H][H].C1(C=CC(O)=CC=1)O>[C].[Pd]>[NH2:1][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

8

Reactant 6

HCID 785HydroquinoneHCID 67041-Nitroanthraquinone2×HCID 67059,10-Anthracenedione, 1,5-dinitro-HCID 14798Sodium HydroxideHCID 672101,8-Dinitro-9,10-anthraquinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 67101-AminoanthraquinoneYield 97.4%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Conditions

Temperature
30 °C

Procedure

A 500 ml. electromagnetically stirred flask was charged with 5.0 g of crude 1-nitroanthraquinone having a purity of 97% and containing 2% of 1,5-dinitroanthraquinone and 1% of 1,8-dinitroanthraquinone as impurities (0.0l92 mole of 1-nitroanthraquinone, and 0.005 mole of all the dinitroanthraquinones), 100 g (0.1 mole) of a 4% aqueous solution of sodium hydroxide and 0.1 g of 5% palladium-carbon. The inside of the flask was purged with hydrogen, and at a reaction temperature of 30° C., they were stirred. In 3 hours, the reaction was stopped with the absorption of 0.08 mole of hydrogen. The amount of hydrogen absorbed was slightly in excess of the sum of the amount of hydrogen required to convert the nitro group to an amino group (0.0606 mole) and the amount of hydrogen required to convert 1-aminoanthraquinone to its hydroquinone derivative (0.0192 mole). The inside of the flask was purged with nitrogen, and the reaction mixture was filtered in an atmosphere of nitrogen to separate the catalyst. The filtrate was oxidized with air at 20° to 30° C. for 2 hours with stirring to afford 4.2 g of 1-aminoanthraquinone in a yield of 97.4% of theory. The product had a purity of 99% as determined by infrared absorption spectroscopy.

Workup

  1. customThe inside of the flask was purged with hydrogen
  2. customThe amount of hydrogen absorbed
  3. customThe inside of the flask was purged with nitrogen
  4. filtrationthe reaction mixture was filtered in an atmosphere of nitrogen
  5. customto separate the catalyst
  6. waitThe filtrate was oxidized with air at 20° to 30° C. for 2 hours
  7. stirringwith stirring

Sources & evidence

ORD record
ord-9bc872d6daec4f4a807b833faff29f5d
Source dataset
uspto-grants-1977_10
Patent number
US04054586

Linked notes

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