o-(p-Nitrophenoxy)anisole → 4-(2-methoxyphenoxy)aniline

HRID 1796674Notes

Reaction equation

HRID 1796674 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 122965o-(p-Nitrophenoxy)anisole

Product 1

HCID 11210674-(2-methoxyphenoxy)anilineYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 430A (7.34 g, 29.9 mmol) and 10% Pd/C (1.47 g, 20 wt %, 50 wt % H2O) was stirred under H2 balloon in MeOH (60 ml) for 12 h. The catalyst was removed by filtration on celite. The filtrate was concentrated in vacuo to give 430B (6.40 g, 99%) as a white solid. It has a retention time of 3.77 min (standard ∠Cl method, 8 min run). MS found: (M+H)+=216.1

Workup

  1. customThe catalyst was removed by filtration on celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a137a8ed4f30446c8bd2c87653e3b74c
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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