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Short Paper | Regular issue | Vol 89, No. 8, 2014, pp.1885-1891
Published online, 20th June, 2014
DOI: 10.3987/COM-14-13023
A New and Practical Synthesis of 7-(3-Chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Yongjun Mao, Jianfeng Qin, Haijun He, Gang Liu, Bingyi Gao, and Han Wang*

*Department of Medicinal Chemistry, Shanghai University of Engineering Science, 333 Longteng Rd., Songjiang, Shanghai, 201620, China

Abstract

New and improved synthetic route of bosutinib intermediate 7-(3-chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile (3) is described on a hectogram scale. An intramolecular cyclization of 3-(2-aminophenyl)-3-oxopropanenitrile 11 with DMF-DMA to form the 4-oxo-1,4-dihydroquinoline-3-carbonitrile ring is adopted as the key step. Product 3 is obtained with 29.8% yield over eight steps and 98.6% purity (HPLC), which make it as a process of cost effective, environmental friendly and feasible for scale-up operation.