1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 972997Notes

Reaction equation

HRID 972997 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.[OH-].[Na+].[H][H]>[Ni]>[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

5

Reactant 3

HCID 67041-Nitroanthraquinone2×HCID 14798Sodium HydroxideHCID 178418361HCID 178418361, compound

Product 1

HCID 67101-AminoanthraquinoneYield 94.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A 160 ml. electromagnetically stirred autoclave was charged with 2.53 g (0.01 mole) of 1-nitroanthraquinone (roughly purified product with no impurity detected by thin-layer chromatography), 52 g (0.05 mole) of a 4% aqueous solution of sodium hydroxide and 0.07 g of Raney nickel. The 1-nitroanthraquinone was hydrogenated with stirring at room temperature and a pressure of 6 to 3 Kg/cm2. G. The reaction proceeded smoothly, and stopped in 6 hours with the absorption of 0.04 mole of hydrogen. The inside of the autoclave 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 1 hour with stirring to afford 2.1 g of 1-aminoanthraquinone having a purity of 97% by weight in a yield of 94% of theory. By a thin layer chromatographic analysis, no impurity was detected in the resulting product.

Workup

  1. customThe inside of the autoclave was purged with nitrogen
  2. filtrationthe reaction mixture was filtered in an atmosphere of nitrogen
  3. customto separate the catalyst
  4. stirringwith stirring

Sources & evidence

ORD record
ord-91179ca756774b5bb2a90d424531420b
Source dataset
uspto-grants-1977_10
Patent number
US04054586

Reaction notes

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