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Short Paper | Regular issue | Vol 89, No. 5, 2014, pp.1203-1209
Published online, 27th March, 2014
DOI: 10.3987/COM-13-12830
New Synthesis of N-(4-Chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide

Yongjun Mao, Yang He, Fuqiang Zhu, Weiming Chen, Jingshan Shen, and Jianfeng Li*

*Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, 501 Haike Rd, Shanghai 201203, China

Abstract

New synthetic route of N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide (1) is described on a hectogram scale. The key steps include the intramolecular cyclization of 3-amino-2-(2-chlorobenzoyl)acrylonitrile 22 to give the 3-cyano-4-quinolone 7, which was chlorinated by POCl3 to give the final product 1 in 36.9% yield over 9 steps and 98.9% purity (HPLC). Purification methods of 7 and 1 were also given.