HCID 21292556, compound → 1-Aminoanthraquinone

HRID 1730998Notes

Reaction equation

HRID 1730998 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.[H][H]>[Pd].C(O)CCC>[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 2

HCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67101-AminoanthraquinoneYield 89.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

0.07 Gram of 5% palladium on carbon catalyst was added to a mixture of 7.7 grams of 5-nitrotetrahydroanthraquinone and 240 grams of butanol, which was then heated up to 50° C. Hydrogen was then fed into the solution under normal pressure to absorb hydrogen in an amount of 2 mols per mol of the starting 5-nitro compound. After separation of the catalyst by filtration, 4.0 grams of crystal sodium carbonate was added to the reaction solution while agitating at a temperature of 100° C. for 1 hour. Thereafter, hydrochloric acid was added to the reaction solution for neutralization, then butanol was distilled off from the solution until crystals began to precipitate. After allowing to cool, the reaction solution was filtered and the crystals were washed with water and dried to obtain 6.0 grams of 1-aminoanthraquinone having a purity of 97.2%.

Workup

  1. customto absorb hydrogen in an amount of 2 mols per mol of the starting 5-nitro compound
  2. customAfter separation of the catalyst
  3. filtrationby filtration, 4.0 grams of crystal sodium carbonate
  4. additionwas added to the reaction solution
  5. additionThereafter, hydrochloric acid was added to the reaction solution for neutralization
  6. distillationbutanol was distilled off from the solution until crystals
  7. customto precipitate
  8. temperatureto cool
  9. filtrationthe reaction solution was filtered
  10. washthe crystals were washed with water
  11. customdried

Sources & evidence

ORD record
ord-11dd59d2fe34448296cd0f0dd45da2e8
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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