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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

Write the mechanism of the reaction shown in Figure 21-9 between coenzyme A and acetyl adenylate to give acetyl CoA.

If the following molecule is treated with acid catalyst, an intramolecular esterification reaction occurs. What is the structure of the product? (Intramolecular means within the same molecule.)

Outline methods for the preparation of acetophone(Phenyl methyl ketone) starting from the following:

a)Benzene b) Bromobenzene c) Methyl benzoate

d) Benzonitrile e) Styrene

21-37 Fats are biosynthesized from glycerol 3-phosphate and fatty-acyl CoA'sby a reaction sequence that begins with the following step. Show the mechanism of the reaction.

21-43 The following reaction, called the benzilic acid rearrangement, takes place by typical carbonyl group reactions. Propose a mechanism (Ph=phenyl).
See all solutions

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