Acetic Acid → 1-Aminoanthraquinone

HRID 1065029Notes

Reaction equation

HRID 1065029 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1C(O)=O.C(O)(=O)C.C(=O)=O>[Zn].O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 280Carbon DioxideHCID 67012-Anthracenecarboxylic acid, 1-amino-9,10-dihydro-9,10-dioxo-

Product 1

HCID 67101-AminoanthraquinoneYield 112%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To a three-necked round-bottomed flask equipped with stirrer and reflux condenser was added 5 g (0.014 mole) 1-aminoanthraquinone-2-carboxylic acid, 1 g (0.0037 mole) zinc powder, and 40 ml of 90% acetic acid. The mixture was refluxed gently for 4 hours during which time carbon dioxide was evolved. The reaction mixture was then poured into 200 ml of water and the resulting mixture was heated on a steam bath for 30 minutes. The red solid which precipitated was collected by filtration and washed with water to give 3.5 g (82% yield) of more than 90% pure 1-aminoanthraquinone.

Workup

  1. customTo a three-necked round-bottomed flask equipped with stirrer
  2. temperaturereflux condenser
  3. temperaturethe resulting mixture was heated on a steam bath for 30 minutes
  4. customThe red solid which precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-ea9fa8669d0142a58b90ef9a6f270319
Source dataset
uspto-grants-1982_05
Patent number
US04328161

Reaction notes

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