42835-89-2

white to yellowish crystalline low melting solid

Intermediate in the production of anti-cancer quinoline derivatives and antibacterial agents

General procedure for the synthesis of 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline from 6-fluoro-2-methylquinoline: in a round-bottomed flask, pre-dried in an oven, a magnetic stirrer was added, followed by the sequential addition of 6-fluoro-2-methylquinoline (0.1 mmol), PCCP (1 mol%), Hantzsch dihydropyridine (3.0 equiv), and CHCl3 (2 mL). The reaction mixture was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography with the eluent of hexane/EtOAc (20:1, v/v) to afford the target product 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline.

[1] Synlett, 2008, # 6, p. 900 - 902
[2] Tetrahedron Letters, 2017, vol. 58, # 21, p. 2050 - 2053
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 11, p. 1183 - 1187
[4] Chemistry - A European Journal, 2015, vol. 21, # 14, p. 5370 - 5379
[5] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724