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.

中文翻译：

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一种新的和改进的方法ñ - （4-氯-3-氰基-7-乙氧基喹啉-6-基）乙酰胺

以千克规模描述了一种新的和改进的合成路线，以合成N-（4-氯-3-氰基-7-乙氧基喹啉-6-基）乙酰胺（1）。关键步骤是邻-[（2-氰基乙烯基）氨基]苯甲酸酯（14）在^t BuONa / ^t BuOH体系中的基本环化，得到3-氰基-4-羟基喹啉（7）。最终产品1的总收率（七个步骤）为49％，纯度（HPLC）为98.9％，这使其成为规模经济的经济高效且商业友好的工艺。