White Paper: The Synthesis Of 3-Methyl Salicylic Acid [ring-14C(U)]

BY Analytical Bio-Chemistry Laboratories (ABC Labs)

3-Methyl salicylic acid is an important precursor for the synthesis of many biologically active species. For example, Moreau reported the synthesis of a series of aryhydrazones and evaluated their vitro antifungal properties against two human pathogenic yeasts. 3-Methyl salicylic acid was also used for the synthesis of aurintricarboxylic acid which was tested for prevention of the cytopathic effects of HIV-1 and HIV-2 in MT-4 cell culture, and HIV-1 in CEM cell culture. Some non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the alkenyldiarylmethane (ADAM) series were also synthesized from 3-methyl salicylic acid.

3-Methyl salicylic acid [ring-14C(U)] was required as a key intermediate to prepare [14C] labeled drug candidates. The key steps are the ortho-methylation of acetanilide [ring-14C(U)] mediated by palladium acetate and the ortho-carboxylation of o-cresol MOM ether [ring-14C(U)].