1-Nitro-4-phenoxybenzene → (4-Aminophenoxy)benzene

HRID 411994Notes

Reaction equation

HRID 411994 reaction equation
[CH:1]1[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>[Ni].CO>[O:7]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 121101-Nitro-4-phenoxybenzene

Product 1

HCID 8764(4-Aminophenoxy)benzeneYield 99.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-Nitrodiphenyl ether (3.92 g, 18 mmol) was hydrogenated over Raney nickel (1.5 g) in methanol (100 mL) at 25° C. at 50 psi for 2 hours. The reaction mixture was celite filtered, and the volatiles were stripped rigourously under reduced pressure to give 4-phenoxyaniline (3.32 g, 97.6%) as an off-white solid.

Sources & evidence

ORD record
ord-ee03114346144c99913c2919fff15fce
Source dataset
uspto-grants-2003_05
Patent number
US06562818B1

Reaction notes

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