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Vicarious nucleophilic substitution: a dramatically shortened synthesis of 2-amino-6-nitrobenzoic acid labelled with carbon-14

✍ Scribed by Terence P. Kelly; Crist N. Filer; Christopher Wright


Book ID
102368361
Publisher
John Wiley and Sons
Year
2011
Tongue
French
Weight
164 KB
Volume
54
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

Literature preparations of 2‐amino‐6‐nitrobenzoic acid are usually based on phthalic anhydride. In order to make [benzene‐^14^C(U)]‐2‐amino‐6‐nitrobenzoic acid, [benzene‐^14^C(U)]‐phthalic anhydride has to be prepared in multiple steps from [^14^C(U)]‐benzene, resulting in an unacceptably lengthy 14‐step synthesis. We have been able to develop a completely different method of synthesis, producing [benzene‐^14^C(U)]‐2‐amino‐6‐nitrobenzoic acid from [^14^C(U)]‐benzene in just four steps with an overall radiochemical yield of 32%. Copyright © 2011 John Wiley & Sons, Ltd.