Prodrugs are molecules which will react in the biological system to release the active ingredient of a drug. Carboxylic acids in drug molecules are often derivatized as esters to increase their lipophilicity and the ester will be hydrolyzed in the stomach acid when the medication is taken orally. You are tasked to make the ethyl ester prodrug of tolfenamic acid, a nonsteroidal anti-inflammatory drug. You use the following procedure: A mixture of tolfenamic acid (1 equiv.), ethanol (15 mL) and H2SO4 (0.35 equiv.) are heated to reflux for 30 min. After cooling and performing the liquid-liquid extraction, you isolate a solid with a melting point of 207 °C. This does not match the expected value for tolfenamic ethyl ester. What is the structure (drawn) of the isolated compound? Draw a full arrow-pushing mechanism explaining why the Fischer esterification did not work and propose a procedural modification to allow for the synthesis of the desired tolfenamic acid ethyl ester.
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