Sodium Hydroxide → 1,2-Diaminoanthraquinone

HRID 2071317Notes

Reaction equation

HRID 2071317 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].C1(C)C=CC=CC=1>[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

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 425969,10-Anthracenedione, 1,2-dinitro-2×HCID 178418361HCID 178418361, compound

Product 1

HCID 156521,2-DiaminoanthraquinoneYield 97.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

A 500 ml. electromagnetically stirred glass reactor was charged with 5.0 g of dinitroanthraquinone (a mixture of 1,5-isomer and 1,8-isomer), 50 g of a 4% aqueous solution of sodium hydroxide, 50 g of toluene and 0.25 g of 5% palladium-carbon, and the dinitroanthraquinone was hydrogenated with stirring at a pressure of 40 to 30 Kg/cm2.G and a temperature of 40° to 50° C. The reaction was stopped in 5 hours with the absorption of 0.1169 mole of hydrogen. 50 g of a 4% aqueous solution of sodium hydroxide was added, and the reaction mixture was filtered in a stream of nitrogen to separate the catalyst. The filtrate was separated into an aqueous pahse and a toluene phase. The aqueous phase was oxidized with air with stirring at 20° to 30° C. for 2 hours. The crystals precipitated were filtered and dried to afford 3.9 g of diaminoanthraquinone in a yield of 97.5%.

Workup

  1. customa temperature of 40° to 50° C
  2. filtrationthe reaction mixture was filtered in a stream of nitrogen
  3. customto separate the catalyst
  4. customThe filtrate was separated into an aqueous pahse
  5. stirringwith stirring at 20° to 30° C. for 2 hours
  6. customThe crystals precipitated
  7. filtrationwere filtered
  8. customdried

Sources & evidence

ORD record
ord-b4fd8480359d4b7a97ce84af64371f1b
Source dataset
uspto-grants-1977_09
Patent number
US04046785

Reaction notes

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