Hydrochloric Acid → 3-[5-(4-Cyano-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid

Participants

Reaction Conditions

Reaction Steps

Suspend of 3-[5-(4-cyano-phenyl)[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid methyl ester (0.120 g, 0.376 mmol) in 4 mL of a 1:1 mixture of H2O:MeOH. Heat the mixture to 60° C., and add 10% aqueous solution of NaOH (0.28 mL, 0.70 mmol). Stir at 60° C. for 30 minutes, cool to room temperature and adjust the pH to 5 by the addition of a 2 N solution of HCl. Concentrate the mixture overnight under a stream of air, dilute crude residue with H2O and extract with methylene chloride. Wash the combined organic phase with brine, dry over anhydrous sodium sulfate and concentrate to provide 0.11 g 4% yield of 3-[5-(4-cyano-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid as a white solid.

Provenance & Evidence