Ammonia → 3,3'-Diaminobenzophenone

HRID 2290973Notes

Reaction equation

HRID 2290973 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[C:4]([N+]([O-])=O)[C:3]=1[N+:19]([O-])=O.[H][H].[NH3:24]>[Pd].C(O)C>[NH2:19][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:2]=1)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:24])[CH:9]=1)=[O:7]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 54185359HCID 54185359, compound2×HCID 178418361HCID 178418361, compound4×

Product 1

HCID 691453,3'-DiaminobenzophenoneYield 72.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

30.7 g (0.1 mol) of this crude chlorodinitrobenzophenone, 0.31 g of 5% Pd/C (a product of Nippon Engelhardt K.K.) and 200 ml of ethanol were charged in a closed glass vessel equipped with a thermometer and a stirrer. While vigorously stirring the mixture at 45±2° C., hydrogen was introduced thereinto and 11.76 l(0.525 mol) of hydrogen was absorbed in 7 hours. The reaction mixture was cooled to 30±2° C. and 11 g of 28% aqueous ammonia was added thereto. Hydrogen was introduced at the same temperature and 3.84 l (0.17 mol) of hydrogen was absorbed in 5 hours. After the completion of the reaction, the temperature of the reaction mixture was raised to 75° to 80° C. The catalyst and contaminants were removed by filtering the reaction mixture with heating. The filtrate was cooled to precipitate 3,3'-diaminobenzophenone as a yellow crystal. The crystal was recovered by filtration, washed with a 50% aqueous ethanol solution, and dried to give 15.3 g (yield 72.2% based on the crude chlorodinitrobenzophenone) of a product with m.p. of 148° to 149.5° C. This product was recrystallized from water to give pure 3,3'-diaminobenzophenone as a light yellow needle crystal with m.p. of 149° to 150° C.

Workup

  1. customequipped with a thermometer and a stirrer
  2. temperatureThe reaction mixture was cooled to 30±2° C.
  3. customwas absorbed in 5 hours
  4. customAfter the completion of the reaction
  5. temperaturethe temperature of the reaction mixture was raised to 75° to 80° C
  6. customThe catalyst and contaminants were removed
  7. filtrationby filtering the reaction mixture
  8. temperaturewith heating
  9. temperatureThe filtrate was cooled
  10. customto precipitate 3,3'-diaminobenzophenone as a yellow crystal
  11. filtrationThe crystal was recovered by filtration
  12. washwashed with a 50% aqueous ethanol solution
  13. customdried
  14. customto give 15.3 g (yield 72.2%
  15. customThis product was recrystallized from water

Sources & evidence

ORD record
ord-3718d3344fee48128ba555f487b6028e
Source dataset
uspto-grants-1986_10
Patent number
US04618714

Reaction notes

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