Q21-72E - Organic Chemistry (Mcmurry)

Question

21-72 Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthesis of this compound starting from 4-nitrosalicylic acid.

Step-by-Step Solution

Answer

The following is the synthesis of 4-aminosalicylate from 4-nitrosalicylic acid,

Step 1: Introduction to the Concept

Chemical synthesis is the method of reworking a reactant or beginning material into a product or many products through appearing one or greater chemical reactions.

Step 2: Solution Explanation

When 4-nitrosalicylic acid is treated with thionyl chloride eliminates , it produces 4-nitrosalicyl chloride, which is then transformed into ae phenolic ster when exposed to phenol. The nitro group of the ester is converted to an amino group when it is treated with , resulting in 4-aminosalicylate.

The following is a formula for making 4-aminosalicylate from 4-nitrosalicylic acid.