2-Methyl-4-nitro-1-phenoxybenzene → 3-Methyl-4-phenoxyaniline

HRID 1592819Notes

Reaction equation

HRID 1592819 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 186166912-Methyl-4-nitro-1-phenoxybenzene

Product 1

HCID 155504883-Methyl-4-phenoxyaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-4-nitro-1-phenoxybenzene and 10% Pd/C (3.35 g) were dissolved in 200 mL EtOH and stirred under 1 atmosphere of H2 overnight. The reaction mixture was filtered through Celite with the aid of 50 mL EtOH and concentrated to provide 3-methyl-4-phenoxybenzenamine as an oil, which was used in Step C without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite with the aid of 50 mL EtOH
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e9ee4c09cd5b4058a2ce01362df76e76
Source dataset
uspto-grants-2007_11
Patent number
US07294616B2

Reaction notes

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