Synthesis of phenyl-3- and phenyl-5-acetamidosalicylates as potential analgesics

Phenylsalicylate was nitrated to obtain two nitro isomers, which were separated and reduced to the corresponding amines followed by acetylation to give phenyl-5- or phenyl-3-acetamidosalicylate. Phenyl-5-acetamidosalicylate displayed analgesic activity comparable to that of aspirin and phenacetin at doses of 25-50 mg/kg sc and was much less toxic than the latter compounds. Phenyl-3-acetamidosalicylate, however, was ineffective at a similar dose range and caused restlessness at larger doses.