Sodium Hydroxide → 3,3'-Diaminobenzophenone

HRID 637548Notes

Reaction equation

HRID 637548 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1Cl)[C:7]([C:9]1[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-])=O)[CH:10]=1)=[O:8])([O-])=O.[H][H].[OH-].[Na+]>[Pd].O1CCOCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:16])[CH:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 3483014,4'-Dichloro-3,3'-dinitrobenzophenoneHCID 178418361HCID 178418361, compound3×

Product 1

HCID 691453,3'-Diaminobenzophenone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a closed glass vessel equipped with a thermometer and a stirrer, there are added 102 g (0.3 moles) of 3,3'-dinitro-4,4'-dichloro benzophenone, 5 g of 5% palladium/active carbon catalyst (available from Nihon Engelhardt Co.) and 300 ml of dioxane. While the mixture is being stirred at 70°-80° C., hydrogen is introduced in the vessel so that 41.5 l (1.85 moles) of hydrogen is absorbed into the mixture over 8 hours. After addition of 80 g (0.8 moles) of 40% aqueous sodium hydroxide, hydrogen is again introduced to the vessel with the mixture being stirred at 70°-80° C., so that it is absorbed 13.8 l (0.62 moles) over 3 hours. The reaction solution is filtered at 70°-80° C. to remove the catalyst. On cooling the solution, there is obtained 3,3'-diamino benzophenone, as yellow needle-like crystals. The crystals are filtered, washed with 30 ml of 50% aqueous solution of dioxane and dried. Yield 59.2 g (93%). M.P. 149°-151° C.

Workup

  1. customTo a closed glass vessel equipped with a thermometer and a stirrer, there
  2. customis absorbed into the mixture over 8 hours
  3. additionis again introduced to the vessel with the mixture
  4. stirringbeing stirred at 70°-80° C., so that it
  5. customis absorbed 13.8 l (0.62 moles) over 3 hours
  6. filtrationThe reaction solution is filtered at 70°-80° C.
  7. customto remove the catalyst
  8. temperatureOn cooling the solution

Sources & evidence

ORD record
ord-e6ecfb5e17d74705ae657c0e1a1bbc07
Source dataset
uspto-grants-1985_12
Patent number
US04556738

Reaction notes

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