Sodium Hydroxide → 1-Aminoanthraquinone

HRID 1283447Notes

Reaction equation

HRID 1283447 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]=[CH:8][C:9]2=[O:14])([O-])=O.[N+]([C:19]1[CH:20]=C2C(=[CH:27][CH:28]=1)C(=O)C=CC2=O)([O-])=O.[OH-].[Na+].[H][H]>[Pd]>[NH2:1][C:4]1[C:5]2[C:6](=[O:15])[C:7]3[C:8](=[CH:20][CH:19]=[CH:28][CH:27]=3)[C:9](=[O:14])[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 54551NitronaphthoquinoneHCID 123364025-Nitronaphthalene-1,4-dioneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67101-AminoanthraquinoneYield 94.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

25.7 Grams (0.1 mol) of crude 5-nitrotetrahydroanthraquinone obtained by condensing in ethanol 1,3-butadiene and 5-nitro-1,4-naphthoquinone containing therein 10% of 6-nitro-1,4-naphthoquinone was placed in a reactor having an inner volume of 2 liters together with 514 grams (0.13 mol) of a 1% aqueous sodium hydroxide solution and 0.52 gram of a 5% palladium on carbon catalyst and was hydrogenated with hydrogen at room temperature and under normal pressure with agitation. The hydrogenation reaction was stopped when 0.2 mol of hydrogen was abosrbed. Into the resultant reaction solution was fed air for oxidizing the over-reduced compound formed. The resultant reaction product was separated by filtration together with the catalyst. The thus separated product was mixed with N,N-dimethylformamide for dissolving the product alone, followed by separation of the catalyst by filtration. The resultant filtrate was diluted with water for precipitation to obtain 21 grams of 1-aminoanthraquinone containing therein 2% of 2-aminoanthraquinone (at a yield of 94.2%).

Workup

  1. customThe hydrogenation reaction
  2. customInto the resultant reaction solution
  3. customformed
  4. customThe resultant reaction product
  5. customwas separated by filtration together with the catalyst
  6. additionThe thus separated product was mixed with N,N-dimethylformamide
  7. dissolutionfor dissolving the product alone
  8. customfollowed by separation of the catalyst by filtration
  9. additionThe resultant filtrate was diluted with water for precipitation

Sources & evidence

ORD record
ord-407e025e273841e792493828d15fd657
Source dataset
uspto-grants-1976_08
Patent number
US03975411

Reaction notes

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