(4-Chloro-3-nitrophenyl)(4-nitrophenyl)methanone → Hydrochloric Acid

HRID 637553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637553
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[N+:19]([O-])=O.[H][H]>[Pd].C1C=CC=CC=1>[ClH:1].[NH2:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:2]=1)[C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)=[O:7]

Komponenten

6

Edukt 2

HCID 554735(4-Chloro-3-nitrophenyl)(4-nitrophenyl)methanoneHCID 178418361HCID 178418361, Verbindung2×

Produkt 2

HCID 313Hydrochloric AcidHCID 148536(3-Aminophenyl)(4-aminophenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

In a closed glass vessel equipped with a thermometer and a stirrer there are charged 30.7 g (0.1 moles) of 4-chloro-3,4'-dinitro benzophenone, 1 g of palladium black catalyst and 300 ml of benzene. While the mixture being stirred, at 65°-70° C., hydrogen is introduced so that 13.3 l (0.59 moles) of hydrogen is absorbed in the mixture during about nine hours. After there are added 45 g (0.12 moles) of 15% aqueous solution of sodium hydroxide and 2 g of 90% aqueous solution of trioctyl methyl ammonium chloride (available from Tokyo-Kasei Co.), hydrogen is again introduced so that 2.35 l (0.105 moles) is absorbed during about six hours, while the mixture being stirred at 65°-70° C. The reaction mixture is filtered to remove the catalyst and organic layer is separated. The organic layer is added with magnesium sulfate for water removal and then blown with hydrochloric gas to saturation therewith. The precipitate thus formed is filtered, washed with 50 ml of benzene, and dried to obtain hydrochloric acid salt form of 3,4'-diamino benzophenone. Yield 23.4 g (82%). Recrystallization from 20% aqueous isopropanol gives yellow needle-like pure crystals of the benzophenone. M.P. is 250° C. or higher.

Aufarbeitung

  1. customIn a closed glass vessel equipped with a thermometer and a stirrer there
  2. customis absorbed in the mixture during about nine hours
  3. additionAfter there are added 45 g (0.12 moles) of 15% aqueous solution of sodium hydroxide and 2 g of 90% aqueous solution of trioctyl methyl ammonium chloride (available from Tokyo-Kasei Co.), hydrogen
  4. additionis again introduced so that 2.35 l (0.105 moles)
  5. customis absorbed during about six hours, while the mixture
  6. stirringbeing stirred at 65°-70° C
  7. filtrationThe reaction mixture is filtered
  8. customto remove the catalyst and organic layer
  9. customis separated
  10. additionThe organic layer is added with magnesium sulfate for water removal
  11. customThe precipitate thus formed
  12. filtrationis filtered
  13. washwashed with 50 ml of benzene
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0c85419f685a484caf0dac4bd1f1f5dc
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04556738

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