3846-73-9

基本信息
4-甲基-8-羥基喹啉
4-Methylquinolin-8-o
4-Methylquinolin-8-ol
4-Methyl-8-quinolinol
8-Quinolinol, 4-Methyl-
4-METHYL-8-HYDROXYQUINOLINE
8-hydroxy-4-methylquinoline
物理化學(xué)性質(zhì)
制備方法

78-94-4

95-55-6

3846-73-9
將37%鹽酸(45.5 mL)和鄰氨基苯酚(10.91 g,0.1 mol)加入250 mL二頸圓底燒瓶中,充分?jǐn)嚢璨⒓訜嶂?20℃。緩慢滴加甲基乙烯基酮(14.32 mL,0.175 mol),保持回流反應(yīng)6小時。反應(yīng)完成后,冷卻至室溫,用氫氧化鈉水溶液中和反應(yīng)混合物。隨后,用二氯甲烷(50 mL × 3)進(jìn)行萃取。合并有機(jī)相,用無水硫酸鎂干燥,減壓濃縮除去溶劑。粗產(chǎn)物通過硅膠柱色譜純化,以二氯甲烷為洗脫劑。最后,用二氯甲烷與正己烷(1:1,v/v)混合溶劑重結(jié)晶,得到無色固體4-甲基-8-羥基喹啉(4.38 g,產(chǎn)率27.5%)。核磁共振氫譜(400 MHz, (CD3)2CO, Me4Si)數(shù)據(jù)如下:δ 8.68(d, 1H, J = 4.4 Hz),7.55(dd, 1H, J1 = 8.4 Hz, J2 = 1.5 Hz),7.51(dd, 1H, J1 = 8.4 Hz, J2 = 7.2 Hz),7.41(dd, 1H, J1 = 4.4 Hz, J2 = 0.8 Hz),7.12(dd, 1H, J1 = 7.2 Hz, J2 = 1.5 Hz),2.71(d, 3H, J = 0.8 Hz)。
參考文獻(xiàn):
[1] Chemical Communications, 2015, vol. 51, # 84, p. 15458 - 15461
[2] Journal of the Chinese Chemical Society, 2004, vol. 51, # 4, p. 735 - 742
[3] Tetrahedron Letters, 2016, vol. 57, # 25, p. 2797 - 2799
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 3986
[5] Patent: US4843082, 1989, A