Ammonia → Benzenamine, 3,3'-methylenebis-

HRID 1719636

Reaction equation

HRID 1719636 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)([O-])=O.[H][H].N>[Pd].C(O)C>[CH:13]1[CH:12]=[C:11]([NH2:16])[CH:10]=[C:9]([CH2:7][C:6]2[CH:19]=[CH:20][CH:21]=[C:4]([NH2:1])[CH:5]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 3483014,4'-Dichloro-3,3'-dinitrobenzophenoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 146486Benzenamine, 3,3'-methylenebis-Yield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

34.1 g (0.1 mol) of 3,3'-dinitro-4,4'-dichlorbenzophenone, 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 50° to 60° C., hydrogen was introduced thereinto and 22.9 l (1.02 mol) of hydrogen was absorbed in 7.5 hours. Since no more absorption of hydrogen was observed, the reaction was terminated at this point. The reaction solution was neutralized with 13.4 g (0.22 mol) of 28% aqueous ammonia and filtered to remove the catalyst. The filtrate was concentrated to give 3,3'-diaminodiphenylmethane as a brown oil. A high performance liquid chromatography revealed that the purity was 93.8%.

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 remove the catalyst
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f4816608550245f69547883a4064a4b6
Source dataset
uspto-grants-1985_09
Patent number
US04540818

Linked notes

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