Synthesis
3-Benzyl-6-bromo-2-chloroquinoline (20 g, 0.06 mol) was dissolved in anhydrous methanol (100 mL), followed by the addition of a methanolic solution of 15% sodium methanolate (108 g). The reaction mixture was refluxed overnight with stirring. Upon completion of the reaction, the mixture was cooled to room temperature and stored at -20 °C overnight to induce precipitation of the product. The crude product 3-benzyl-6-bromo-2-methoxyquinoline precipitated as white needle-like crystals. The solid product was separated by filtration, washed with water and dried in air to give 19 g (96% yield) of the target compound as a white solid.
References
[1] ChemMedChem, 2017, vol. 12, # 2, p. 106 - 119
[2] Tetrahedron, 2007, vol. 63, # 2, p. 451 - 460
[3] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 790 - 792
[4] Patent: WO2005/70430, 2005, A1. Location in patent: Page/Page column 34-35
[5] Patent: WO2006/67048, 2006, A1. Location in patent: Page/Page column 27
