4,4'-Dichloro-3,3'-dinitrobenzophenone → 3,3'-Diaminobenzophenone

HRID 637547Notes

Reaction equation

HRID 637547 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.[O-2].[Ca+2].[H][H]>[Pd].ClCCCl>[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 3483014,4'-Dichloro-3,3'-dinitrobenzophenoneHCID 6850728CalciumoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 691453,3'-Diaminobenzophenone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To an autoclave there are added 50 g (0.15 moles) of 3,3'-dinitro-4,4'-dichloro benzophenone, 21 g (0.38 moles) of calcium oxide, 1 g of 5% palladium/alumina catalyst (available from Nihon-Engelhardt Co., Ltd.) and 350 ml of 1,2-dichloro ethane. The reaction is carried out for ten hours by introducing hydrogen into the autoclave, with the mixture being stirred at 30°-35° C., to keep the pressure at 10 Kg/cm2.G. After the completion of the reaction, the reaction mixture is heated up to 70° C. and subjected to a hot filtering so as to remove the catalyst and the inorganic salt. On cooling the mixture there are obtained yellow needle-like crystals of 3,3'-diamino benzophenone. The crystals are filtered, washed with 10 ml of 1,2-dichloro ethane and dried. Yield 21.2 g (67%). M.P. 149°-150.5° C. Recrystallization from ethanol gives pure crystals. M.P. 150°-151° C.

Workup

  1. waitThe reaction is carried out for ten hours
  2. customAfter the completion of the reaction
  3. filtrationa hot filtering so as
  4. customto remove the catalyst
  5. temperatureOn cooling the mixture there

Sources & evidence

ORD record
ord-320100a0c75c4b7296d3cb6866d9835d
Source dataset
uspto-grants-1985_12
Patent number
US04556738

Reaction notes

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