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Convenient Novel Method to Access N‑Benzylated Isatoic Anhydride: Reaction Behavior of Isatoic Anhydride with 4‑Chlorobenzyl Chloride in the Presence of Bases
Sodium hydride, potassium carbonate, and other bases are commonly used for N-alkylation of heterocyclic compounds. This report reveals the problems associated with N-benzylation of isatoic anhydride and identifies the plausible byproduct structures formed during the reaction. Subsequently, a novel b...
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Published in: | ACS omega 2021-03, Vol.6 (12), p.8346-8355 |
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Main Authors: | , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | Sodium hydride, potassium carbonate, and other bases are commonly used for N-alkylation of heterocyclic compounds. This report reveals the problems associated with N-benzylation of isatoic anhydride and identifies the plausible byproduct structures formed during the reaction. Subsequently, a novel breakthrough methodology has been developed using diisopropylamine and tetra butyl ammonium bromide. It gives excellent yields >88% in a short reaction time (2 h) at 30 °C with no byproducts, saving on processes as the pure product is directly obtained. |
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ISSN: | 2470-1343 2470-1343 |
DOI: | 10.1021/acsomega.1c00061 |