4-(4-Nitrophenoxy)-1,1'-biphenyl → 4-(4-Phenylphenoxy)aniline

HRID 17730Notes

Reaction equation

HRID 17730 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1>CCOC(C)=O.[Pd]>[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 2408644-(4-Nitrophenoxy)-1,1'-biphenyl

Product 1

HCID 2471244-(4-Phenylphenoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The nitro intermediate (10 mmol) obtained above was dissolved in EtOAc (40 mL) and hydrogenated in the presence of 10% Pd/C (360 mg) until completion, as indicated by TLC or HPLC. The reaction mixture was then filtered to remove the catalyst. The solvent was removed in vacuo to afford the desired 4-(biphenyl-4-oxy)aniline, which was used directly for further transformation without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customto remove the catalyst
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b3531b0ff9884950a75d8d04e43a9bc4
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Reaction notes

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