1-Methyl-4-(methyloxy)-2-[(4-nitrophenyl)oxy]benzene → 4-{[2-Methyl-5-(methyloxy)phenyl]oxy}aniline

HRID 1023514Notes

Reaction equation

HRID 1023514 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1>CO.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 672359211-Methyl-4-(methyloxy)-2-[(4-nitrophenyl)oxy]benzene2×

Product 1

HCID 672359714-{[2-Methyl-5-(methyloxy)phenyl]oxy}anilineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-methyl-4-(methyloxy)-2-[(4-nitrophenyl)oxy]benzene (Intermediate 13, 2.5 g) and Pd/C (10%, 1 g) in MeOH (100 mL) was stirred under H2 atmosphere for overnight at room temperature and filtered through a pad of celite. The filtrate was evaporated to afford the title compound as a solid (2.0 g).

Workup

  1. filtrationfiltered through a pad of celite
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-70820af988a144289ad960f6bc7cca0a
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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