5622-36-6
5622-36-6 結構式
基本信息
6-喹啉乙酸甲酯
喹啉-6-乙酸甲酯
METHYL 6-QUINOLINEACETATE
methyl quinolin-6-ylacetate
Methyl 2-quinolin-6-ylacetate
Methyl 6-quinolineacetate ,95%
6-Quinolineacetic acid methyl ester
Quinolin-6-Yl-Acetic Acid Methyl Ester
物理化學性質(zhì)
制備方法
67-56-1
5622-34-4
5622-36-6
實施例1. 喹啉-6-乙酸甲酯的制備：如方案1的步驟i所示，將濃硫酸（206 mL，3.868 mol）緩慢滴加到溶解于6.5 L甲醇中的6-喹啉乙酸（化合物1001，658.2 g，3.516 mol，Okeanos Tech Co.，目錄號OK-J-05024）溶液中。滴加過程中觀察到輕微放熱。滴加完畢后，將反應混合物在回流條件下攪拌4小時。反應完成后，冷卻至室溫，減壓蒸餾除去揮發(fā)性溶劑。殘余物用4 L乙酸乙酯稀釋，并在冰浴中冷卻。隨后，用2 N NaOH溶液（2.1 L，1.2當量）調(diào)節(jié)pH至4，再用飽和碳酸氫鈉溶液調(diào)節(jié)pH至8。分離有機層和水層，水層用乙酸乙酯萃取兩次。合并的有機相依次用飽和碳酸氫鈉溶液、水和鹽水洗滌，然后用無水MgSO4干燥。過濾后，減壓蒸發(fā)溶劑，得到喹啉-6-乙酸甲酯（化合物1002，696.8 g，收率98%）為透明棕色油狀物：ESMS (M + 1), 202.14; 1H NMR (300.0 MHz, DMSO-d6) δ 8.90 (1H, dd, J = 1.7, 4.2 Hz), 8.14-8.10 (1H, m), 8.08 (1H, d, J = 8.7 Hz), 7.72 (1H, d, J = 1.4 Hz), 7.65 (1H, dd, J = 2.0, 8.7 Hz), 7.40 (1H, dd, J = 4.2, 8.3 Hz), 3.83 (2H, s), 3.73 (3H, s)。
參考文獻：
[1] Patent: WO2010/59668, 2010, A1. Location in patent: Page/Page column 20-21
[2] Patent: WO2016/8011, 2016, A1. Location in patent: Page/Page column 67
[3] Patent: WO2013/19682, 2013, A1. Location in patent: Page/Page column 117
[4] Patent: WO2008/144767, 2008, A1. Location in patent: Page/Page column 110; 115
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6651 - 6665