1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 973001

Reaktionsgleichung

Reaktionsgleichung von HRID 973001
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[N+](C1C2C(=O)C3C(=C([N+]([O-])=O)C=CC=3)C(=O)C=2C=CC=1)([O-])=O.[N+](C1C2C(=O)C3C(=CC=CC=3[N+]([O-])=O)C(=O)C=2C=CC=1)([O-])=O.C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.[OH-].[Na+].[H][H]>[C].[Pd].CO>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

9

Edukt 6

HCID 67041-Nitroanthraquinone3×HCID 67059,10-Anthracenedione, 1,5-dinitro-HCID 6780AnthraquinoneHCID 14798Sodium HydroxideHCID 672101,8-Dinitro-9,10-anthraquinoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67101-AminoanthraquinoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A 500 ml. electromagnetically stirred autoclave was charged with 10 g of 1-nitroanthraquinone having a purity of 91.5% and containing 7.0% of 1,5-dinitroanthraquinone, 0.5% of 1,8-dinitroanthroquinone and 1.0% of anthraquinone as impurities, 120 g of a 3% aqueous solution of sodium hydroxide (0.01 mole as sodium hydroxide), 80 g of methanol, and 200 mg of 5% palladium-carbon (2% based on the 1-nitroanthraquinone). The 1-nitroanthraquinone was hydrogenated at a temperature of 50° C. and a pressure of 40 to 30 Kg/cm2.G. In 60 minutes, 0.16 mole of hydrogen was absorbed, whereupon the reaction was stopped. The inside of the autoclave was purged with nitrogen, and 80 g of a 3% aqueous solution of sodium hydroxide was added. Methanol was distilled off at reduced pressure (60 to 70 mmHg abs.) and 40 to 50° C. Then, the reaction mixture was suction-filtered in a stream of nitrogen to remove the catalyst and the diaminoanthraquinones. The filtrate was oxidized with air at 20 to 30° C. for 2 hours with stirring to afford 7.65 g of 1-aminoanthraquinone having a purity of 98% in a yield of 93% of theory.

Aufarbeitung

  1. customwas hydrogenated at a temperature of 50° C.
  2. customThe inside of the autoclave was purged with nitrogen, and 80 g of a 3% aqueous solution of sodium hydroxide
  3. additionwas added
  4. distillationMethanol was distilled off at reduced pressure (60 to 70 mmHg abs.) and 40 to 50° C
  5. filtrationThen, the reaction mixture was suction-filtered in a stream of nitrogen
  6. customto remove the catalyst
  7. waitThe filtrate was oxidized with air at 20 to 30° C. for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-4af893a741ef4904995f0a023caf9232
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04054586

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