3-Methyl-2-nitroanisole → 2-Methoxy-6-methylaniline

HRID 1358939Notes

Reaction equation

HRID 1358939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[N+:10]([O-])=O>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10]

Participants

4

Reactant 1

HCID 792913-Methyl-2-nitroanisole

Product 1

HCID 4592492-Methoxy-6-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-methoxy-3-methyl-2-nitrobenzene (15.04 g, 0.09 mol) in ethanol (250 ml) was hydrogenated over 10% palladium on charcoal (4 g) at atmospheric pressure and at room temperature, for 18 h. The catalyst was removed by filtration, and the filtrate evaporated under reduced pressure to leave the title compound (D28) as an amber oil, which crystallised on standing (11.18 g, 91%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-6d7e7e529731450082821b906b6e9160
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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