Sodium Hydroxide → 1,2-Diaminoanthraquinone

HRID 2071312Notes

Reaction equation

HRID 2071312 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[C:5]=1[N+:20]([O-])=O)([O-])=O.[OH-].[Na+].[H][H]>[C].[Pd]>[NH2:1][C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:19])[C:6]=2[C:5]=1[NH2:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 425969,10-Anthracenedione, 1,2-dinitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 156521,2-DiaminoanthraquinoneYield 98%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

A 500 ml. electromagnetically stirred glass reactor was charged with 5.0 g (0.0167 mole) of dinitroanthraquinone (a mixture of 1,5-isomer and 1,8-isomer), 100 g (0.1 mole) of a 4% aqueous solution of sodium hydroxide and 0.25 g of 5% palladium-carbon. The inside of the reactor was purged with hydrogen, and the dinitroanthraquinone was hydrogenated at 30° C. with stirring. In 5 hours, 0.1169 mole of hydrogen was absorbed, the reaction was stopped. The reaction mixture was filtered in an atmosphere of nitrogen to separate the catalyst. Then, the filtrate was oxidized with air with stirring at 20° to 30° C. for 2 hours. The resulting crystals were filtered and dried to afford 3.9 g of diaminoanthraquinone (a mixture of 1,5-isomer and 1,8-isomer) in a yield of 97.5%.

Workup

  1. customThe inside of the reactor was purged with hydrogen
  2. customwas hydrogenated at 30° C.
  3. filtrationThe reaction mixture was filtered in an atmosphere of nitrogen
  4. customto separate the catalyst
  5. stirringwith stirring at 20° to 30° C. for 2 hours
  6. filtrationThe resulting crystals were filtered
  7. customdried

Sources & evidence

ORD record
ord-66190b0bac3540ceb1333c108bd123d4
Source dataset
uspto-grants-1977_09
Patent number
US04046785

Reaction notes

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