HCID 17755138, compound → 3,4,4'-Triaminodiphenyl ether

HRID 1294056Notes

Reaction equation

HRID 1294056 reaction equation
FC1C=CC(C(F)(F)F)=CC=1NC([NH:15][C:16]1[CH:32]=[CH:31][C:19]([O:20][C:21]2[CH:22]=[CH:23][C:24]([N+:28]([O-])=O)=[C:25]([CH:27]=2)[NH2:26])=[CH:18][CH:17]=1)=O>C(O)C.[Pd]>[CH:32]1[C:16]([NH2:15])=[CH:17][CH:18]=[C:19]([O:20][C:21]2[CH:22]=[CH:23][C:24]([NH2:28])=[C:25]([NH2:26])[CH:27]=2)[CH:31]=1

Participants

4

Reactant 1

HCID 17755138HCID 17755138, compound2×

Product 1

HCID 804343,4,4'-Triaminodiphenyl ether

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C (5%, 3.0 g) was introduced to a solution of 5-(4-((2-Fluoro-5-(trifluoromethyl)phenyl)aminocarbonylamino)phenoxy)-2-nitroaniline (Intermediate 5) (21.6 g, 48 mmol) in ethanol (200 ml) under Ar. The starting material was hydrogenated under a H2 atmosphere for 3 days while being stirred. The reaction mixture was then filtered through celite and evaporated to give intermediate 6 as a black film. This crude material was chromatographed through silica gel (hexane-AcOEt, 4:1–3:1–2:1–1:1–0:1) to give purified intermediate 6 (13.0 g, 64%): MS m/e 421 (M+1).

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-31589d8c46b547bab248aa95a080c06e
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

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