Chemical Properties
Melting point 42-43℃, boiling point 269-270℃, 83℃ (93Pa), relative density 0.881, refractive index 1.6224. Slightly soluble in water.
Synthesis
General procedure: 4-hydroxy-2-methylquinoline (5a-c) was added to POCl3 and the reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, the excess POCl3 was removed by distillation under reduced pressure. the residue was washed once and twice each with CHCl3 and toluene sequentially. The solid obtained was dissolved in CH2Cl2 and triethylamine was added dropwise until the pH of the aqueous wash solution was greater than 10. Finally, the reaction mixture was filtered to afford the target products 2-methyl-4-chloroquinoline (6a-c).
References
[1] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 1114 - 1125
[2] Patent: US2008/171765, 2008, A1. Location in patent: Page/Page column 19-20
[3] Australian Journal of Chemistry, 2003, vol. 56, # 1, p. 39 - 44
[4] Letters in Drug Design and Discovery, 2018, vol. 15, # 9, p. 937 - 944
[5] Patent: WO2018/178277, 2018, A1. Location in patent: Paragraph 00114
