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

Participants

Reaction Steps

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.

Provenance & Evidence