Convenient Novel Method to Access N‑Benzylated
Isatoic Anhydride: Reaction Behavior of Isatoic
Anhydride with 4‑Chlorobenzyl Chloride in the Presence of Bases
posted on 2021-03-16, 20:30authored byEkta Verma, Shailendra Patil, Asmita Gajbhiye
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.