Sodium Hydroxide → 1-Aminoanthraquinone

HRID 1283444Notes

Reaction equation

HRID 1283444 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, compound3×

Product 1

HCID 67101-AminoanthraquinoneYield 94.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2.6 Grams (0.01 mol) of 5-nitrotetrahydroanthraquinone, 52 grams (0.013 mol) of a 1% aqueous sodium hydroxide solution, and 0.052 grams of a 5% palladium on carbon catalyst were introduced into an electromagnetic agitation-type glass reactor having an inner volume of 200 ml. Then, the atmosphere in the reactor was replaced by hydrogen, followed by hydrogenation while agitating at room temperature. When 0.015 mol of hydrogen was absorbed, the hydrogen in the system was replaced by nitrogen and then by air for oxidizing the resultant over-reduced compound while agitating for 30 minutes. The resultant reaction product was separated together with the catalyst by filtration and was dissolved in N,N-dimethylformamide for separating the catalyst by filtration. To the resultant filtrate was added water for dilution to obtain 2.1 grams of 1-aminoanthraquinone (at a yield of 93.1%). The purity of the 1-aminoanthraquinone was 98%.

Workup

  1. stirringwhile agitating for 30 minutes
  2. customThe resultant reaction product
  3. customwas separated together with the catalyst by filtration
  4. dissolutionwas dissolved in N,N-dimethylformamide
  5. customfor separating the catalyst
  6. filtrationby filtration
  7. additionTo the resultant filtrate was added water for dilution

Sources & evidence

ORD record
ord-52e6b9bdf4154490879116dde029b841
Source dataset
uspto-grants-1976_08
Patent number
US03975411

Reaction notes

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