1-Methoxy-4-methyl-2-nitrobenzene → 2-Methoxy-5-Methylaniline

HRID 1603401

Reaction equation

HRID 1603401 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1>C(O)C.[Pd]>[NH2:10][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

4

Reactant 1

HCID 670581-Methoxy-4-methyl-2-nitrobenzene

Product 1

HCID 84452-Methoxy-5-Methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-methyl-2-nitroanisole (Aldrich) (10 g, 0.06 mol) in 100 ml of absolute ethanol was hydrogenated in the presence of 0.25 g of Pd/C (10%) at room temperature. The catalyst was removed by filtration and the clear solution was concentrated to give 2-amino -4-methylanisole as a white solid. To this solid was added 70 ml of acetic anhydride and a few drops of concentrated sulfuric acid. After stirring for 1 h, the mixture was poured into ice/water and the precipitated product was filtered and dried to give 9.48 g (88%) of S1 as a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe clear solution was concentrated

Sources & evidence

ORD record
ord-daa5bbffff194a29a3faafae28876b13
Source dataset
uspto-grants-1999_11
Patent number
US05989451

Linked notes

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