Hydrochloric Acid → 3-Methoxy-2-methyl-6-nitroaniline

Participants

Reaction Steps

Sodium methoxide in methanol (110 mL of 25% solution, 0.49 mol, 20 equiv) was added to a stirred suspension of 3-chloro-2-methyl-6-nitrobenzenamine (4.0 g, 23.5 mmol) in methanol (250 mL) and the mixture was stirred at reflux for 18 hours. The solution was cooled, neutralized with methanolic hydrogen chloride, filtered to remove sodium chloride, and the solvent was removed under reduced pressure. The residual solid was partitioned between ethyl acetate and water. Evaporation of the ethyl acetate gave 3.7 g (86%) of 3-methoxy-2-methyl-6-nitrobenzenamine.

Provenance & Evidence