1-Methoxy-2-methyl-4-nitrobenzene → 3-Methyl-4-methoxybenzenamine

HRID 931741Notes

Reaction equation

HRID 931741 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[CH3:12].[H][H]>CCO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[CH3:12]

Participants

6

Reactant 2

HCID 6435201-Methoxy-2-methyl-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 672973-Methyl-4-methoxybenzenamineYield 99.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 1-methoxy-2-methyl-4-nitrobenzene (10 g, 60 mmol) in EtOH and EtOAc (250 mL, 3:2) was added 10% Pd/C (2 g). The mixture was stirred for 24 h under one atmosphere of hydrogen. Celite was added and the mixture was stirred for 10 min. The mixture was filtered through a pad of celite. Concentration under reduced pressure gave 4-methoxy-3-methylaniline (8B) (8.2 g). LCMS-ESI+ (m/z): 138.2 (M+H)+.

Workup

  1. additionCelite was added
  2. filtrationThe mixture was filtered through a pad of celite
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-b7d03db8e4f947fd859e7815f4502e78
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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