Question

The following compound is one of a group of \(\beta\)-chloroamines, many of which have antitumor activity. Describe a synthesis of this compound from anthranilic acid and ethylene oxide. O=C1OCCN(CCCl)c2ccccc21 2-Aminobenzoic acid A \(\beta\)-chloramine (Anthranilic acid)

Short answer

Question: Describe a synthesis of a β-chloroamine compound with antitumor activity using anthranilic acid and ethylene oxide as starting materials. Answer: The synthesis can be done in three steps: 1) Activation of anthranilic acid by converting the carboxylic acid into an acid chloride using thionyl chloride, resulting in 2-chlorocarbonylaminobenzene. 2) Formation of a cyclic structure called an isatoic anhydride by reacting the activated anthranilic acid with ethylene oxide. 3) Formation of the β-chloroamine compound through the addition of chloroethylamine and an excess of ethylene oxide to the isatoic anhydride, leading to a ring-opening reaction.

Step-by-step solution

Activation of Anthranilic Acid

Activate the carboxylic acid group of anthranilic acid by converting it into a more reactive species. This can be done by converting the carboxylic acid into an acid chloride using thionyl chloride (SOCl2). Upon reaction, we will obtain an intermediate, 2-chlorocarbonylaminobenzene.

Ring Formation

Introduce ethylene oxide to the activated anthranilic acid. The electrophilic carbon of the activated acid chloride will react with the nucleophilic oxygen of ethylene oxide, forming a cyclic structure called an isatoic anhydride.

Formation of β-chloroamine

In the final step, add chloroethylamine (CClwith an excess of ethylene oxide to the isatoic anhydride. The nucleophilic nitrogen of the ethylene oxide will attack the carbonyl carbon of the isatoic anhydride, leading to ring-opening and formation of the final product, the β-chloroamine compound. And there you have the synthesis of the target β-chloroamine compound starting from anthranilic acid and ethylene oxide.