2,2-bis[N-(2-nitrophenyl)-(4-aminophenyl)]hexafluoropropane → 2,2-bis[N-(2-aminophenyl)-(4-aminophenyl)]hexafluoropropane

HRID 23972Notes

Reaction equation

HRID 23972 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[N+:39]([O-])=O)=[CH:28][CH:27]=2)([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[C].[Pd]>[NH2:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[NH:32][C:29]1[CH:28]=[CH:27][C:26]([C:17]([C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[NH2:1])=[CH:12][CH:13]=2)([C:22]([F:23])([F:24])[F:25])[C:18]([F:20])([F:21])[F:19])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 225712732,2-bis[N-(2-nitrophenyl)-(4-aminophenyl)]hexafluoropropaneHCID 178418361HCID 178418361, compound

Product 1

HCID 225712682,2-bis[N-(2-aminophenyl)-(4-aminophenyl)]hexafluoropropaneYield 94.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

20 g (34.7 mmol) of 2,2-bis[N-(2-nitrophenyl)-(4-aminophenyl)]hexafluoropropane synthesized above were dissolved in 200 ml of ethyl acetate. Thereto was added 1 g of 10% palladium carbon as a catalyst, and replacement with hydrogen was then carried out. After that, reaction was conducted at room temperature under a hydrogen pressure of 1.01 MPa (10 atm) for 18 hours with stirring vigorously. The obtained reaction solution was filtered with cerite to remove the catalyst, and ethyl acetate was removed under reduced pressure. The residue was re-crystallized by using a chloroform-hexane mixed solution, and ethanol-water mixed solution to obtain 17 g of 2,2-bis[N-(2-aminophenyl)-(4-aminophenyl)]hexafluoropropane (hereinafter pNPN-AF) in white solid (yeild: 95%).

Workup

  1. customAfter that, reaction
  2. customwas conducted at room temperature under a hydrogen
  3. customfor 18 hours
  4. customThe obtained reaction solution
  5. filtrationwas filtered with cerite
  6. customto remove the catalyst, and ethyl acetate
  7. customwas removed under reduced pressure
  8. customThe residue was re-crystallized

Sources & evidence

ORD record
ord-496e69487e88413f89480b77dc4201d0
Source dataset
uspto-grants-2005_02
Patent number
US06855774B2

Reaction notes

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