Ammonium Chloride → Methyl 3-amino-5-chloro-2-hydroxybenzoate

Participants

Reaction Steps

To 100 ml of an aqueous 0.78N ammonium chloride solution (with heating at 85° C.) is added 33.4 g of powdery iron with stirring followed by addition of a solution of 49.1 g of methyl 5-chloro-3-nitrosalicylate in 500 ml of toluene over 30 minutes. The reaction temperature rises to 95° C. The resultant solution is stirred at 80°-90° C. for an hour, and filtered with suction through hot celite. The mother liquor is poured into 1 l of ice-cold water, and the toluene layer is separated, washed with water and dried over magnesium sulfate. The solvent is distilled off and the residue is recrystallized from ethanol to give 25.4 g of methyl 3-amino -5-chlorosalicylate, melting at 65°-67° C.

Provenance & Evidence