(2-Chloro-5-nitrophenyl)(4-chloro-3-nitrophenyl)methanone → 3,3'-Diaminobenzophenone

HRID 637555

Reaction equation

Cl[C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9](Cl)=[C:8]([N+:13]([O-])=O)[CH:7]=1)=[O:5].[H][H].O.N>[Pd].O1CCOCC1>[NH2:13][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:4]([C:3]1[CH:2]=[CH:19][CH:18]=[C:17]([NH2:20])[CH:16]=1)=[O:5]

Participants

Conditions

Temperature: 30 °C

Procedure

In a closed glass vessel with a thermometer and a stirrer, there are charged 102.3 g (0.3 moles) of 2,4'-dichloro-5,3'-dinitro benzophenone, 5 g of 5% palladium/active carbon catalyst (from Nihon-Engelhardt Co.) and 300 ml of dioxane. At 70°-80° C., hydrogen is introduced into the vessel while the mixture being stirred, so that 42 l (1.88 moles) of hydrogen is absorbed in the mixture during ten hours. After being cooled to 30° C., the mixture is added with 55 g (0.9 moles) of 28% ammonia water and then introduced with hydrogen while being stirred at 30°-40° C. so as to absorb 13.2 l (0.59 moles) of hydrogen during 5 hours. The reaction mixture is subject to filtering at 30°-40° C. to remove the catalyst. On cooling, there is obtained 3,3'-diamino benzophenone as yellow crystals. The crystals are filtered, washed with 30 ml of 50% aqueous solution of dioxane and dried. Yield 56.5 g (89%). M.P. 149°-150.5° C. Recrystallization from ethanol gives yellow needle-like pure crystals of said benzophenone. M.P. 150°-151° C.

Workup

customis absorbed in the mixture during ten hours
filtrationto filtering at 30°-40° C.
customto remove the catalyst
temperatureOn cooling

Sources & evidence

ORD record: ord-7c2c2d1a711c48e4859820b5212da161
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04556738

Linked notes

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