Azane;hydrate → 3,3'-Diaminobenzophenone

HRID 637558Notes

Reaction equation

HRID 637558 reaction equation
[N+:1]([C:4]1[C:5]([N+]([O-])=O)=[C:6](Cl)[C:7](Cl)=[C:8]([CH:17]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])([O-])=O.[H][H].O.[NH3:26]>[Pd].O1CCOCC1>[NH2:1][C:4]1[CH:17]=[C:8]([CH:7]=[CH:6][CH:5]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:26])[CH:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 12896473Azane;hydrateHCID 20257109HCID 20257109, compoundHCID 178418361HCID 178418361, compound4×

Product 1

HCID 691453,3'-Diaminobenzophenone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
30 °C

Procedure

Then, in a closed glass vessel equipped with a thermometer and a stirrer, there are charged 34 g (0.1 moles) of said crude dinitro-dichloro benzophenone, 1 g of 5% Pd/C (from Nihon-Engelhardt Co.) and 100 ml of dioxane. While the mixture being stirred at 70°-80° C., hydrogen is introduced into the vessel so that 14.2 l (0.63 moles) of hydrogen is absorbed during 15 hours. After being cooled to 30° C., the mixture is added with 18.2 g (0.3 moles) of ammonia water and then again introduced, while being stirred at 30°-35° C., with hydrogen so as to absorb 4.3 l (0.19 moles) of hydrogen during 8 hours. After completion of reaction, the mixture is heated up to 70° C. for filtering in order to remove the catalyst. On cooling the mixture, there is obtained 3,3'-diamino benzophenone in yellow crystals. The crystals is filtered, washed with 10 ml of 50% aqueous solution of dioxane and dried. Yield 17.6 g (83.0%). M.P. 148.5°-150° C. Recrystallization from ethanol yields slightly yellow needle-like crystals of said diamino benzophenone. M.P. 150°-151° C.

Workup

  1. customThen, in a closed glass vessel equipped with a thermometer and a stirrer, there
  2. additionare charged 34 g (0.1 moles)
  3. customis absorbed during 15 hours
  4. additionagain introduced
  5. customAfter completion of reaction
  6. temperaturethe mixture is heated up to 70° C.
  7. filtrationfor filtering in order
  8. customto remove the catalyst
  9. temperatureOn cooling the mixture

Sources & evidence

ORD record
ord-8ce500d757404d0291b0aaba25d6b791
Source dataset
uspto-grants-1985_12
Patent number
US04556738

Reaction notes

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