Sodium Hydroxide → 1-Aminoanthraquinone

HRID 1283445Notes

Reaction equation

HRID 1283445 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.[OH-].[Na+].[H][H]>[Pd]>[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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67101-AminoanthraquinoneYield 93.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The same amounts of 5-nitrotetrahydroanthraquinone, aqueous sodium hydroxide solution and palladium on carbon catalyst as in Example 1 were placed in a cylindrical glass reactor having an inner volume of 500 ml and equipped with a thermometer, an agitator, a hydrogen inlet and a reflux condenser, into which was fed hydrogen at a flow rate of 1 1/min for hydrogenation while agitating the reaction mixture at room temperature for 6 hours. Thereafter, air for oxidation was fed into the reaction system at a flow rate of 1 1/min for 30 minutes. The resultant reaction product containing therein the catalyst was separated by filtration, followed by dissolution thereof in methyl cellosolve (i.e., β-hydroxyethyl methyl ether) for separating therefrom the catalyst. The resultant filtrate was condensed to obtain 2.1 grams of 1-aminoanthraquinone (at a yield of 93.1%). The purity of the 1-aminoanthraquinone was 98%.

Workup

  1. customequipped with a thermometer
  2. waitThereafter, air for oxidation was fed into the reaction system at a flow rate of 1 1/min for 30 minutes
  3. customThe resultant reaction product
  4. additioncontaining
  5. customthe catalyst was separated by filtration
  6. dissolutionfollowed by dissolution
  7. customin methyl cellosolve (i.e., β-hydroxyethyl methyl ether) for separating
  8. customcondensed

Sources & evidence

ORD record
ord-ee15911c91234005a5bde503d75830c7
Source dataset
uspto-grants-1976_08
Patent number
US03975411

Reaction notes

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