Synthesis
The general procedure for the synthesis of 4-chloro-7-hydroxy-6-methoxy-3-carbonitrile quinoline from the compound (CAS:214476-99-0) is as follows: dissolve the raw material (19.23 g, 60.0 mmol) in trifluoroacetic acid (300 mL), add fennel sulfide (35 mL), and the reaction was carried out under nitrogen protection at reflux for 3 hours. After completion of the reaction, it was cooled to room temperature and the trifluoroacetic acid was removed by rotary evaporator. The oily residue obtained was stirred with ice water and the pH was adjusted to alkaline with concentrated ammonia (specific gravity 0.880). The resulting suspension was filtered and the solid was washed sequentially with water, ethyl acetate and ether and dried to give 13.74 g of khaki colored solid product in 97% yield. Mass spectral analysis showed m/e 235 ([M+H]+).
References
[1] Patent: EP1584619, 2005, A1. Location in patent: Page/Page column 41-42
[2] Patent: US6297258, 2001, B1
[3] Patent: US6288082, 2001, B1
[4] Patent: EP1950201, 2008, A1. Location in patent: Page/Page column 64
[5] Patent: EP1117659, 2003, B1. Location in patent: Page 56
