Calciumoxide → 3,3'-Diaminobenzophenone

HRID 637551

Reaction equation

HRID 637551 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1Cl)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([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:18]=[CH:19][CH:20]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 6850728CalciumoxideHCID 13742658HCID 13742658, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 691453,3'-Diaminobenzophenone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

In an autoclave, there are charged 46 g (0.15 moles) of 3,3'-dinitro-4-chloro benzophenone, 11.2 g (0.2 moles) of calcium oxide, 1 g of 5% palladium/alumina catalyst (available from Nihon-Engelhardt Co.) and 250 ml of 1,2-dichloro ethane. With the mixture being stirred at a temperature of 30°-35° C., the reaction proceeds by the introduction of hydrogen for seven hours under a constant pressure of 10 Kg/cm2.G. After completion of the reaction, the reaction mixture is heated up to 70° C. for hot-filtering so as to remove the catalyst and the inorganic salt. On cooling, there is obtained 3,3'-diamino benzophenone as yellow needle-like crystals. The crystals are filtered, washed with 20 ml of 1,2-dichloro ethane and dried. Yield 24.8 g (78%). M.P. 149°-150° C. Recrystallization from ethanol gives yellow needle-like pure crystals of the benzophenone. M.P. 150°-151° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationfor hot-filtering so as
  3. customto remove the catalyst
  4. temperatureOn cooling

Sources & evidence

ORD record
ord-393fdd5624b94bcea943633e3d048f7e
Source dataset
uspto-grants-1985_12
Patent number
US04556738

Linked notes

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