Sodium Hydroxide → 1-Aminoanthraquinone

HRID 1731006Notes

Reaction equation

HRID 1731006 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:7]=1[C:8](=[O:21])[C:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=1[C:15]2=[O:20])([O-])=O.CC(O)COC(CO)C.[H][H]>[Pd]>[NH2:3][C:6]1[C:7]2[C:8](=[O:21])[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:20])[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 328812-(2-Hydroxypropoxy)-1-propanolHCID 21292556HCID 21292556, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67101-AminoanthraquinoneYield 87.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

0.1 Gram of a 5% palladium on carbon catalyst and 10 grams of a 20% aqueous sodium hydroxide solution were added to a mixture of 12.8 grams of 5-nitrotetrahydroanthraquinone and 170 grams of dipropylene glycol in an autoclave, into which was fed hydrogen, until the pressure reached 25 kg/cm2, for hydrogenation of the 5-nitro compound at 120° C. with agitation. Hydrogen was absorbed in the starting 5-nitro compound in an amount of 2mols per mol of the 5-nitro compound. After completion of the hydrogenation, the resultant solution was subjected to filtration under hot conditions at 120° to 130° C. to remove the catalyst therefrom. To the resultant filtrate was added 350 grams of water for dilution to obtain crystals which were separated by filtration, washed with water and dried to yield 9.7 grams of 1-aminoanthraquinone having a purity of 96.7%.

Workup

  1. customat 120° C.
  2. customHydrogen was absorbed in the starting 5-nitro compound in an amount of 2mols per mol of the 5-nitro compound
  3. filtrationAfter completion of the hydrogenation, the resultant solution was subjected to filtration under hot conditions at 120° to 130° C.
  4. customto remove the catalyst
  5. additionTo the resultant filtrate was added 350 grams of water for dilution
  6. customto obtain crystals which
  7. customwere separated by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-8d5b4e5cb9d049cea28ca84ca9876363
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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