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

HRID 2237051Notes

Reaction equation

HRID 2237051 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-29963977c6fa4a48aefc4b755a27c6fd
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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