1,3-Butadiene → 1-Aminoanthraquinone

HRID 1730996Notes

Reaction equation

HRID 1730996 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].[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

6

Reactant 3

HCID 78451,3-ButadieneHCID 123364025-Nitronaphthalene-1,4-dioneHCID 178418361HCID 178418361, compound2×

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 (i.e., β-hydroxyethyl methyl ether) and 2.4 grams of 1,3-butadiene were introduced into an autoclave and heated to 80° C. for reaction for 2.5 hours. After allowing to cool, 0.06 gram of a 5% palladium on carbon catalyst was added to the solution into which was fed hydrogen while agitating at room temperature under normal pressure for hydrogen absorption in the amount of 2 mols per mol of the starting 5-nitro material. Thereafter, the catalyst was separated by filtration. To the resultant filtrate was added 6 grams of a 20% aqueous sodium hydroxide solution, which was agitated at 60° C. for 1.5 hours for reaction. After completion of the reaction, hydrochloric acid was added to the reaction solution for neutralization, followed by removing methyl cellosolve by distillation under a reduced pressure of 0.2 kg/cm2 for concentration. The thus concentrated solution was allowed to cool thereby to obtain crystals of 1-aminoanthraquinone. After separation by filtration, the crystals were washed with water and dried to obtain 5.6 grams of 1-aminoanthraquinone having a purity of 98.5%.

Workup

  1. temperatureto cool
  2. customThereafter, the catalyst was separated by filtration
  3. additionTo the resultant filtrate was added 6 grams of a 20% aqueous sodium hydroxide solution, which
  4. customAfter completion of the reaction, hydrochloric acid
  5. additionwas added to the reaction solution for neutralization
  6. customby removing methyl cellosolve
  7. distillationby distillation under a reduced pressure of 0.2 kg/cm2
  8. concentrationfor concentration
  9. temperatureto cool

Sources & evidence

ORD record
ord-0c60e1fd0c7d46cfb205d1071885b15f
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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