1,3-Butadiene → 1-Aminoanthraquinone

HRID 1731002Notes

Reaction equation

HRID 1731002 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]=[CH:8][C:9]2=[O:14])([O-])=O.[CH2:16]=[CH:17][CH:18]=[CH2:19].[OH-].[Na+].[H][H]>[Pd].COCCO>[NH2:1][C:4]1[C:5]2[C:6](=[O:15])[C:7]3[C:8](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:9](=[O:14])[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 78451,3-ButadieneHCID 14798Sodium HydroxideHCID 123364025-Nitronaphthalene-1,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
80 °C

Procedure

6.1 Grams of 5-nitro-1,4-naphthoquinone, 140 grams of methyl cellosolve 2.4 grams of 1,3-butadiene were introduced into an autoclave, heated up to 80° C. and reacted for 2.5 hours. After the reaction solution was allowed to cool, 0.06 gram of a 5% palladium on carbon catalyst and 6 grams of a 20% aqueous sodium hydroxide solution were added to the solution, into which was fed hydrogen at room temperature under normal pressure with agitation to absorb hydrogen in the 5-nitro-1,4-naphthoquinone in an amount of 2 mols per mol of the nitro compound. Then, the catalyst was removed by filtration and hydrochloric acid was added to the resultant filtrate for neutralization. From the thus neutralized solution was removed methyl cellosolve by distillation for concentration, followed by allowing to cool to precipitate crystals. The crystals were separated by filtration, washed with water and dried to obtain 5.8 grams of 1-aminoanthraquinone with a purity of 98.7%.

Workup

  1. customreacted for 2.5 hours
  2. temperatureto cool
  3. customat room temperature
  4. customto absorb hydrogen in the 5-nitro-1,4-naphthoquinone in an amount of 2 mols per mol of the nitro compound
  5. customThen, the catalyst was removed by filtration and hydrochloric acid
  6. additionwas added to the resultant filtrate for neutralization
  7. customFrom the thus neutralized solution was removed methyl cellosolve
  8. distillationby distillation
  9. concentrationfor concentration
  10. temperatureto cool
  11. customto precipitate crystals
  12. customThe crystals were separated by filtration
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-64edeeaf15714df58ceb21b0d7ec4aa2
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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