3,3'-Dinitro-4-bromo benzophenone → 3,3'-Diaminobenzophenone

HRID 637550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637550
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1Br)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)=[O:8])([O-])=O.[H][H]>[Pd].O1CCOCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)=[O:8]

Komponenten

5

Edukt 2

HCID 197081953,3'-Dinitro-4-bromo benzophenoneHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 691453,3'-DiaminobenzophenoneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a closed glass vessel equipped with a thermometer and a stirrer, there are charged 105.3 g (0.3 moles) of 3,3'-dinitro-4-bromo benzophenone, 5 g of 5% palladium/active carbon catalyst (available from Nihon-Engelhardt Co.) and 300 ml of dioxane. With the mixture being stirred at 70°-80° C., hydrogen is introduced into the vessel so that 40.5 l (1.81 moles) of hydrogen is absorbed in the mixture over about 8 hours. Then, after 33 g (0.33 moles) of 40% aqueous solution of caustic soda is added, hydrogen is further introduced at 70°-80° C. with the mixture being stirred so that an additional 7.2 l (0.32 moles) is absorbed during three hours. The reaction liquid is filtered at 70°-80° C. so as to remove the catalyst and then allowed to cool giving yellow needle-like crystals of 3,3'-diamino benzophenone. The crystals is filtered, washed with 30 ml of 50% aqueous solution of dioxane, and dried. Yield 93% (59.2 g). M.P. 149°-150° C.

Aufarbeitung

  1. customTo a closed glass vessel equipped with a thermometer and a stirrer, there
  2. customis absorbed in the mixture over about 8 hours
  3. additionThen, after 33 g (0.33 moles) of 40% aqueous solution of caustic soda is added
  4. additionhydrogen is further introduced at 70°-80° C. with the mixture
  5. stirringbeing stirred so that an additional 7.2 l (0.32 moles)
  6. customis absorbed during three hours
  7. customThe reaction liquid
  8. filtrationis filtered at 70°-80° C. so as
  9. customto remove the catalyst
  10. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-e3348361fb3049d7a3bdca156712d455
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04556738

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