Sodium Hydroxide → 1-Aminoanthraquinone

HRID 1283446Notes

Reaction equation

HRID 1283446 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]>[Ni]>[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 94.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

2.6 Grams (0.01 mol) of 5-nitrotetrahydroanthraquinone, 52 grams (0.032 mol) of a 2.5% aqueous sodium hydroxide solution and 0.07 gram of a Raney nickel catalyst were placed in an electromagnetic agitation-type autocalve with an inner volume of 160 ml, followed by hydrogenation while agitating under a pressure of 3 to 6 kg/cm2G at room temperature. The hydrogenation reaction proceeded smoothly. 6 Hours after commencement of the reaction, 0.02 mol of hydrogen was absorbed and the absorption was stopped. Then, the hydrogen in the reaction system was replaced by nitrogen and the resultant reaction solution was filtered in a flow of nitrogen for separating the catalyst therefrom. Air was passed into the resultant filtrate for oxidation to obtain 2.1 grams of 1-aminoanthraquinone (at a yield of 93.1%). The purity was 97%.

Workup

  1. customThe hydrogenation reaction
  2. customwas absorbed
  3. customthe absorption
  4. customthe resultant reaction solution
  5. filtrationwas filtered in a flow of nitrogen
  6. customfor separating the catalyst

Sources & evidence

ORD record
ord-dcb75cf4783645abab9aa74c7cb95690
Source dataset
uspto-grants-1976_08
Patent number
US03975411

Reaction notes

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