Preprint Communication Version 1 Preserved in Portico This version is not peer-reviewed

Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline

Version 1 : Received: 5 March 2024 / Approved: 6 March 2024 / Online: 6 March 2024 (12:02:05 CET)

A peer-reviewed article of this Preprint also exists.

Aparicio Acevedo, D.F.; Ortiz Villamizar, M.C.; Kouznetsov, V.V. Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline. Molbank 2024, 2024, M1796. Aparicio Acevedo, D.F.; Ortiz Villamizar, M.C.; Kouznetsov, V.V. Three-Step Synthesis of N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide from 4,7-Dichloroquinoline. Molbank 2024, 2024, M1796.

Abstract

The quinoline derivative, N-(7-chloro-4-morpholinoquinolin-2-yl)benzamide, was synthesized in a conventional three-step procedure from 4,7-dichloroquinoline using N-oxidation reaction/C2-amidation reaction/C4 SNAr reaction sequence. The structure of the compound was fully characterized by FT-IR, 1H‐, 13C-NMR, DEPT-135°, and ESI-MS techniques. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the online SwissADME database. Such derivatives are relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, and antiparasitic properties.

Keywords

4,7-dichloroquinoline; N-oxides; C–H bond functionalization; C2-amidation reaction; C4 SNAr reaction; N-(quinolinyl)morpholines; N-(quinolinyl)amides; Lipinski’ descriptors

Subject

Chemistry and Materials Science, Organic Chemistry

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