1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 972998Notes

Reaction equation

HRID 972998 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.[H][H].[OH-].[Na+]>[C].[Pd].O>[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

6

Reactant 3

HCID 67041-NitroanthraquinoneHCID 14798Sodium HydroxideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67101-AminoanthraquinoneYield 93.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

A 1-liter electromagnetically stirred glass reactor 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 of water and 0.051 g of 5% palladium-carbon. The inside of the reactor was purged with nitrogen, and with stirring at room temperature, the 1-nitroanthraquinone was hydrogenated. In 4.5 hours when 0.03 mole of hydrogen was absorbed, the hydrogen inside the reactor was replaced by nitrogen, and 2.1 g (0.052 mole) of sodium hydroxide was added. The inside of the reactor was purged with hydrogen, and the hydrogenation was continued at room temperature. In 1 hour, the absorption of hydrogen was stopped. The amount of hydrogen absorbed until then was 0.01 mole. The reaction mixture completely dissolved. The inside of the reactor 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 2.08 g of 1-aminoanthraquinone having a purity of 98% by weight in a yield of 93% of theory. By a thin-layer chromatographic analysis, no impurity was detected.

Workup

  1. customThe inside of the reactor was purged with nitrogen
  2. additionwas added
  3. customThe inside of the reactor was purged with hydrogen
  4. customwas continued at room temperature
  5. customthe absorption of hydrogen
  6. customThe amount of hydrogen absorbed
  7. dissolutionThe reaction mixture completely dissolved
  8. customThe inside of the reactor was purged with nitrogen
  9. filtrationthe reaction mixture was filtered in an atmosphere of nitrogen
  10. customto separate the catalyst
  11. waitThe filtrate was oxidized with air at 20° to 30° C. for 2 hours
  12. stirringwith stirring

Sources & evidence

ORD record
ord-09987efe41884d439acb9cd619db80f6
Source dataset
uspto-grants-1977_10
Patent number
US04054586

Reaction notes

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