2,2-Bis-(4-anilino-3-nitrophenyl)-hexafluoropropane → 2,2-Bis(3-amino-4-anilinophenyl)hexafluoropropane

HRID 1086329Notes

Reaction equation

HRID 1086329 reaction equation
[NH:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:25]([N+:36]([O-])=O)[CH:24]=2)([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[N+:39]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[NH2:36][C:25]1[CH:24]=[C:23]([C:14]([C:11]2[CH:12]=[CH:13][C:8]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]([NH2:39])[CH:10]=2)([C:19]([F:20])([F:21])[F:22])[C:15]([F:17])([F:18])[F:16])[CH:28]=[CH:27][C:26]=1[NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 142050452,2-Bis-(4-anilino-3-nitrophenyl)-hexafluoropropaneHCID 178418361HCID 178418361, compound

Product 1

HCID 142050492,2-Bis(3-amino-4-anilinophenyl)hexafluoropropaneYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

34.6 g (0.06 mol) of 2,2-bis-(4-anilino-3-nitrophenyl)-hexafluoropropane in 220 ml of ethanol are reduced with hydrogen under the catalytic action of 2 g of Pd-on-C (5% by weight in active charcoal) in a 500 ml chromium nickel steel autoclave. The crude product (30.7 g - pure according to H-NMR) is filtered off and recrystallized twice to give 15.1 g of analytically pure 2,2-bis-(3-amino-4-anilinophenyl) -hexafluoropropane (49% yield). The melting point is 177-178° C., and differs from the melting point given in the literature (120° C.).

Workup

  1. filtrationThe crude product (30.7 g - pure according to H-NMR) is filtered off
  2. customrecrystallized twice

Sources & evidence

ORD record
ord-5cf582adc4a943cf9f76389999d15ec6
Source dataset
uspto-grants-1991_07
Patent number
US05028728

Reaction notes

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