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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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Bibliographic Details
Published in:ACS omega 2021-03, Vol.6 (12), p.8346-8355
Main Authors: Verma, Ekta, Patil, Shailendra, Gajbhiye, Asmita
Format: Article
Language:English
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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.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.1c00061