Oxygen → 1-Aminoanthraquinone

HRID 1731001Notes

Reaction equation

HRID 1731001 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+].ONC1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.[H][H].O=O>[Pd].COCCO>[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

8

Reactant 5

HCID 977OxygenHCID 14798Sodium HydroxideHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound3×HCID 178514954HCID 178514954, compound2×

Product 1

HCID 67101-AminoanthraquinoneYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

To a mixture of 260 grams of 5-nitrotetrahydroanthraquinone and 10,100 grams of methyl cellosolve were added 2.6 grams of a 5% palladium on carbon catalyst and 300 grams of a 20% aqueous sodium hydroxide solution, followed by agitating at room temperature for 1 hour. The color of the solution was green inherent to 1-hydroxylaminoanthraquinone. Part of the reaction solution was sampled and subjected to a thin layer chromatography, by which it was recognized that almost all of the starting 5-nitro compound was converted to 1-hydroxylaminoanthraquinone. Thereafter, hydrogen was fed into the reaction solution for hydrogenation and 2 mols of hydrogen was absorbed in each 1 mol of the 5-nitro compound. The hydrogen in the reactor was replaced by nitrogen, followed by introduction of air into the reaction solution for oxidation. Upon determination, it was found that oxygen was absorbed in an amount of 0.5 mol per mol of the 5-nitro compound. The reaction solution turned reddish orange with a reddish orange precipitate. The precipitate was separated by filtration, washed with water and dried to obtain 220 grams of 1-aminoanthraquinone having a purity of 98%.

Workup

  1. aliquotPart of the reaction solution was sampled
  2. customwas absorbed in an amount of 0.5 mol per mol of the 5-nitro compound
  3. customThe precipitate was separated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5594a208acbe4480a9a3a50a31d7a68f
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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