1,3-Butadiene → 1-Aminoanthraquinone

HRID 1731004

Reaktionsgleichung

Reaktionsgleichung von HRID 1731004
[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+].NC1C=CC2C(=O)C3C(=CC=CC=3)C(=O)C=2C=1>[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

Komponenten

7

Edukt 4

HCID 78451,3-ButadieneHCID 83412-AminoanthraquinoneHCID 14798Sodium HydroxideHCID 123364025-Nitronaphthalene-1,4-dione

Produkt 1

HCID 67101-AminoanthraquinoneAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 80192-MethoxyethanolLösungsmittel

Versuchsvorschrift

122 Grams of 5-nitro-1,4-naphthoquinone which contained 10% of the 6-nitro compound, 2,800 grams of methyl cellosolve and 48 grams of 1,3-butadiene were placed in an autoclave, followed by reaction at 90° C. for 2 hours. After allowing to cool, 1.2 grams of a 5% palladium on carbon catalyst and 120 grams of a 20% aqueous sodium hydroxide solution were added to the reaction solution. Then, the procedure of Example 13 was repeated to obtain 108 grams of 1-aminoanthraquinone containing 7% of 2-aminoanthraquinone.

Aufarbeitung

  1. customfollowed by reaction at 90° C. for 2 hours
  2. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-3510745c1520426093b78ee403cf15e4
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03994932

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