A NEW AND PRACTICAL SYNTHESIS OF 7-(3-CHLOROPROPOXY)-6-METHOXY-4-OXO-l,4-DIHYDROQUINOLINE-3-CARBONITRILE

摘要

New and improved synthetic route of bosutinih intermediate 7-(3-chloropropoxy)-6-methoxy-4-oxo-l,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-l,4-dihydroquinoline-3-carbonitrile ring is adopted as the key step. Product 3 is obtained in 29.8% yield over eight steps and 98.6% purity (HPLC), which make it as a process of cost effective, environmentally friendly and feasible for scale-up operation.