Ethanol → Benzenamine, 3,3'-methylenebis-

HRID 1719637Notes

Reaction equation

HRID 1719637 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)([O-])=O.C(O)C.[H][H]>C(O)(C)C.[Pd]>[CH:13]1[CH:12]=[C:11]([NH2:15])[CH:10]=[C:9]([CH2:7][C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([NH2:1])[CH:5]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 13742658HCID 13742658, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 146486Benzenamine, 3,3'-methylenebis-Yield 82.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

30.7 g (0.1 mol) of 3,3'-dinitro-4-chlorobenzophenone, 1.5 g of 5% Pd/C and 100 ml of ethanol were charged in a closed glass vessel equipped with a thermometer and a stirrer. While stirring the mixture at a temperature of 65° to 70° C., hydrogen was introduced thereto and 20.1 l (0.9 mol) of hydrogen was absorbed in 6 hours. Since no more absorption of hydrogen was observed, the reaction was terminated at this point. The reaction mixture was cooled to room temperature and filtered to obtain a black filter cake. This filter cake was dissolved in 100 ml of a 90% aqueous isopropyl alcohol solution with heating. The catalyst was removed by filtration with heating. The filtrate was cooled to precipitate 3,3'-diaminodiphenylmethane hydrochloride as a crystal. This crystal was recovered by filtration, washed with 10 ml of isopropanol and neutralized with dilute aqueous ammonia to precipitate a white crystal. The crystal was recovered by filtration and dried in vacuo to give 16.3 g (yield 82.2%) of 3,3'-diaminodiphenylmethane.

Workup

  1. customequipped with a thermometer and a stirrer
  2. additionwas introduced
  3. customSince no more absorption of hydrogen
  4. customthe reaction was terminated at this point
  5. filtrationfiltered
  6. customto obtain a black filter cake
  7. temperaturewith heating
  8. customThe catalyst was removed by filtration
  9. temperaturewith heating
  10. temperatureThe filtrate was cooled
  11. customto precipitate 3,3'-diaminodiphenylmethane hydrochloride as a crystal
  12. filtrationThis crystal was recovered by filtration
  13. washwashed with 10 ml of isopropanol and neutralized with dilute aqueous ammonia
  14. customto precipitate a white crystal
  15. filtrationThe crystal was recovered by filtration
  16. customdried in vacuo

Sources & evidence

ORD record
ord-efd05a33ec954329973f2d7679443471
Source dataset
uspto-grants-1985_09
Patent number
US04540818

Reaction notes

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