Azane;hydrate → 3,3'-Diaminobenzophenone

HRID 637559Notes

Reaction equation

HRID 637559 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].COCCO>[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 80192-MethoxyethanolSolvent

Conditions

Temperature
30 °C

Procedure

Then, in a closed glass vessel 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 and 100 ml of methyl cellosolve. While stirring the mixture, at 40°-50° C., there is introduced hydrogen so that 13.9 l (0.62 moles) of hydrogen is absorbed in the mixture during twelve hours. Then, the mixture is cooled down to 30° C. and added with 18.2 g (0.3 moles) of 28% ammonia water. There is introduced hydrogen, with the mixture being stirred at 30°-35° C., so that 4.3 l (0.19 moles) of hydrogen is absorbed during five hours. After completion of reaction, the mixture is heated up to 70° C. for hot filtering to remove the catalyst. After being added with 100 ml of hot water, the filtrate is allowed to cool to give yellow crystals of 3,3'-diamino benzophenone. The crystals are filtered, washed with 10 ml of ethanol and dried. Yield 16.8 g (79.2%). M.P. 148°-150° C. Recrystallization from ethanol yields slightly yellow needle-like crystals of the diamino benzophenone. M.P. 150° to 151° C.

Workup

  1. additionThen, in a closed glass vessel with a thermometer and a stirrer, there are charged 34 g (0.1 moles)
  2. customis absorbed in the mixture during twelve hours
  3. customis absorbed during five hours
  4. customAfter completion of reaction
  5. temperaturethe mixture is heated up to 70° C.
  6. filtrationfor hot filtering
  7. customto remove the catalyst
  8. additionAfter being added with 100 ml of hot water
  9. temperatureto cool

Sources & evidence

ORD record
ord-fd39662a81334a2fba1b52bdf0665d6f
Source dataset
uspto-grants-1985_12
Patent number
US04556738

Reaction notes

Loading…