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Chapter 21: Q21-72E (page 726)

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.

Short Answer

Expert verified

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

Step by step solution

01

 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.

02

Step 2: Solution Explanation

When4-nitrosalicylic acid is treated with thionyl chloride eliminates , it produces 4-nitrosalicyl chloride, which is then transformed into aephenolicster when exposed to phenol. Thenitro group of the ester is converted to an amino groupwhen it is treated with , resulting in 4-aminosalicylate.

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

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Most popular questions from this chapter

Kevlar, a nylon polymer prepared by reaction of 1,4-benzenedicarboxylic acid (terephthalic acid) with 1,4-benzenediamine (p-phenylenediamine), is so strong that it鈥檚 used to make bulletproof vests. Draw the structure of a segment of Kevlar.

Given IUPAC names for the following substances:

Why is the saponification of an ester irreversible? In other words, why doesn鈥檛 treatment of a carboxylic acid with an alkoxide ion yield an ester?

How could you prepare the following ketones by reaction of an acid chloride with a lithium diorganocopper reagent?

When an amide is formed from an acid chloride or an anhydride, two moles of base are required. However, when an ester is used as the starting material, only one equivalent of base is needed. Explain the reactivity in terms of basicity of the leaving groups.
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