Sodium Carbonate → 1-Aminoanthraquinone

HRID 1731005Notes

Reaction equation

HRID 1731005 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[N+:7]([C:10]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:11]=1[C:12](=[O:25])[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=1[C:19]2=[O:24])([O-])=O.[H][H]>[Pd].C(O)CCC>[NH2:7][C:10]1[C:11]2[C:12](=[O:25])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19](=[O:24])[C:20]=2[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67101-AminoanthraquinoneYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

0.07 Gram of 5% palladium on carbon catalyst and 8 grams of crystal sodium carbonate were added to a mixture of 7.7 grams of 5-nitrotetrahydroanthraquinone and 320 grams of butanol. The resultant mixture was heated to 70° C. and hydrogen was fed for hydrogenation under normal pressure to have hydrogen absorbed in the starting 5-nitro compound in an amount of 2 mols per mol of the 5-nitro compound. The resultant solution was heated to 100° C. and subjected to filtration under hot conditions for separation of the catalyst therefrom, followed by distilling off butanol for condensation. The condensed solution was allowed to cool to precipitate crystals, which were then separated by filtration, washed with water and dried to obtain 6.1 grams of 1-aminoanthraquinone having a purity of 98.5%.

Workup

  1. customabsorbed in the starting 5-nitro compound in an amount of 2 mols per mol of the 5-nitro compound
  2. filtrationsubjected to filtration under hot conditions for separation of the catalyst
  3. distillationby distilling off butanol
  4. customfor condensation
  5. temperatureto cool
  6. customto precipitate crystals, which
  7. customwere then separated by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-091b04e6475142ec940a1f2ec2b956b4
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

Loading…