1,3-Butadiene → 1-Aminoanthraquinone

HRID 1730997Notes

Reaction equation

HRID 1730997 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]>[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

5

Reactant 2

HCID 78451,3-ButadieneHCID 123364025-Nitronaphthalene-1,4-dione

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

122 Grams of 5-nitro-1,4-naphthoquinone which contained 10% of the 6-nitro compound, 2800 grams of methyl cellosolve and 48 grams of 1,3-butadiene were charged into an autoclave and reacted at 90° C. for 2 hours. The reaction solution was allowed to stand for cooling and 1.2 grams of a 5% palladium on carbon catalyst was added thereto. Thereafter, the procedure of Example 4 was repeated to obtain 104 grams of 1-aminoanthraquinone containing therein 7% of 2-aminoanthraquinone.

Workup

  1. additionwere charged into an autoclave
  2. customreacted at 90° C. for 2 hours
  3. temperaturefor cooling

Sources & evidence

ORD record
ord-906b1acc81a04cdb8bb92c73eeeb88c7
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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