5965-59-3

基本信息
4-羥基-2-喹啉羧酸甲酯
Kynurenic acid, methyl ester
Methyl 4-hydroxyquinaldinate
Methyl 4-hydroxy-2-quinolinecarboxylate
Methyl 4-Hydroxyquinoline-2-carboxylate
methyl 4-oxo-1H-quinoline-2-carboxylate
4-oxo-1H-quinoline-2-carboxylic acid methyl ester
2-Quinolinecarboxylic acid, 4-hydroxy-, methyl ester
物理化學(xué)性質(zhì)
常見(jiàn)問(wèn)題列表

67-56-1

492-27-3

5965-59-3
將4-羥基喹啉-2-羧酸(500 mg, 2.65 mmol)懸浮于無(wú)水甲醇中,緩慢加入濃硫酸(96%,40滴)至溶液澄清。將反應(yīng)混合物加熱至回流,保持回流狀態(tài)反應(yīng)24小時(shí)(通過(guò)LC-MS監(jiān)測(cè)反應(yīng)進(jìn)度,直至起始原料完全消失)。反應(yīng)完成后,冷卻至室溫。使用旋轉(zhuǎn)蒸發(fā)器除去溶劑,得到粗產(chǎn)物。將粗產(chǎn)物溶于甲醇(1 mL)中,加入去離子水(10 mL)稀釋。隨后,緩慢加入飽和碳酸氫鈉溶液,直至白色沉淀析出。過(guò)濾收集沉淀,并用二乙醚洗滌,得到白色固體產(chǎn)物,收率65%(0.35 g)。產(chǎn)物經(jīng)1H NMR(DMSO-d6, 500 MHz)和LC-MS(ES+)表征:1H NMR δ 3.52(s, 3H), 6.48(s, 1H), 7.25(t, 1H, J = 7.0 Hz), 7.58(t, 1H, J = 7.0 Hz), 7.96(d, 1H, J = 8.5 Hz), 8.05(d, 1H, J = 8.5 Hz), 11.32(s, 1H); LC-MS m/z 204.09 [M+H]+, 計(jì)算值204.06。
參考文獻(xiàn):
[1] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 559 - 562
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 20, p. 5453 - 5463
[3] Patent: WO2012/6068, 2012, A2. Location in patent: Page/Page column 67-68
[4] Monatshefte fuer Chemie, 1921, vol. 42, p. 100
[5] Monatshefte fuer Chemie, 1922, vol. 43, p. 479