Methanol → Methyl p-aminosalicylate

Participants

Reaction Steps

4-Aminosalicyclic acid (1 g, 98 mmol) was dissolved in MeOH. HCl(g) was bubbled through until the solution was saturated. The reaction mixture was heated at 70° for 16 hours. Additional MeOH was added to the reaction and saturated again with HCl (g). The reaction was heated at 70° for another 16 hours. The reaction mixture was neutralized with saturated NaHCO3 and extracted with EtOAc. The resulting solid was recrystallized from hot 2:1 hexane/EtOAc and collected on a frit. The solid was further purified by flash chromatography eluting the product with 2/1 hexane/EtOAc to give 4-aminosalicyclic acid methyl ester as a solid.

Provenance & Evidence