A New and Improved Process for N-(4-Chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide

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• 作者：Yongjun Mao ; Zheng Liu ; Xiaojun Yang ; Xiangfei Xia ; Rongxia Zhang ; Jianfeng Li ; Xiangrui Jiang ; Kai Xie ; Jin Zheng ; Hui Zhang ; Jin Suo ; Jingshan Shen
• 刊名：Organic Process Research & Development
• 出版年：2012
• 出版时间：December 21, 2012
• 年：2012
• 卷：16
• 期：12
• 页码：1970-1973
• 全文大小：183K
• 年卷期：v.16,no.12(December 21, 2012)
• ISSN：1520-586X

文摘

A new and improved synthetic route to N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide (1) is described on a kilogram scale. The key step is the basic cyclization of o-[(2-cyanovinyl)amino]benzoate (14) in ^tBuONa/^tBuOH system to give the 3-cyano-4-hydroxyquinoline (7). The final product 1 is obtained with 49% overall yield (seven steps) and 98.9% purity (HPLC), which makes it a cost-effective and commercially friendly process for scale-up operations.