Oxygen → 1-Aminoanthraquinone

HRID 1730995Notes

Reaction equation

HRID 1730995 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:19])[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=1[C:13]2=[O:18])([O-])=O.[H][H].O=O>[Pd].C(O)C>[NH2:1][C:4]1[C:5]2[C:6](=[O:19])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13](=[O:18])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 977OxygenHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67101-AminoanthraquinoneYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.13 Gram of a 5% palladium on carbon catalyst was added to a mixture of 13 grams of 5-nitrotetrahydroanthraquinone and 1200 grams of ethanol, and hydrogen was fed into the resultant mixture for absorption in an amount of 3 mols per mol of the 5-nitro compound at room temperature and under atmospheric pressure. The solution was first pale yellow in color, and then gradually turned yellowish brown and finally pale yellow again. Then, after the hydrogen in the reactor was replaced by nitrogen, 20 grams of a 20% sodium hydroxide solution was added to the reaction solution, the color of which immediately turned dark reddish brown through dark reddish purple and a small amount of glossy crystals were precipitated. The reaction was completed rapidly and air was fed into the reaction solution for oxidation. Upon determination, it was found that 1 mole of oxygen was absorbed per mol of the 5-nitro compound. As a result of the oxidation, the reaction solution turned reddish orange with reddish orange-colored crystals being precipitated. The resultant solution was subjected to filtration, followed by extraction of the resultant cake with acetone for separation of the catalyst. The resultant filtrate was dried to obtain 11 grams of 1-aminoanthraquinone having a purity of 95%.

Workup

  1. customwas fed into the resultant mixture for absorption in an amount of 3 mols per mol of the 5-nitro compound at room temperature and under atmospheric pressure
  2. additionwas added to the reaction solution
  3. customthe color of which immediately turned dark reddish brown through dark reddish purple and a small amount of glossy crystals were precipitated
  4. customwas absorbed per mol of the 5-nitro compound
  5. customAs a result of the oxidation
  6. custombeing precipitated
  7. filtrationThe resultant solution was subjected to filtration
  8. extractionfollowed by extraction of the resultant cake with acetone
  9. customfor separation of the catalyst
  10. dry with materialThe resultant filtrate was dried

Sources & evidence

ORD record
ord-f6fd8d007de849778d46c254b5aac69d
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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