2,2-bis[N-(2-nitrophenyl)-(3-aminophenyl)]hexafluoropropane → 2,2-bis[N-(2-aminophenyl)-(3-aminophenyl)]hexafluoropropane

HRID 23975Notes

Reaction equation

HRID 23975 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:12]=[C:13]([C:17]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[N+:39]([O-])=O)[CH:27]=2)([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=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:28]1[CH:27]=[C:26]([C:17]([C:13]2[CH:14]=[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]=2)([C:22]([F:23])([F:24])[F:25])[C:18]([F:20])([F:21])[F:19])[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 225712742,2-bis[N-(2-nitrophenyl)-(3-aminophenyl)]hexafluoropropaneHCID 178418361HCID 178418361, compound

Product 1

HCID 225712672,2-bis[N-(2-aminophenyl)-(3-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)-(3-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 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 recrystallized by using a chloroform-hexane mixed solution, and ethanol-water mixed solution to obtain 17 g of 2,2-bis[N-(2-aminophenyl)-(3-aminophenyl)]hexafluoropropane (hereinafter mNPN-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 recrystallized

Sources & evidence

ORD record
ord-655801eb68994f7cb45eaff222468b67
Source dataset
uspto-grants-2005_02
Patent number
US06855774B2

Reaction notes

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