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(4a) 4-Hydroxy-2-methylquinoline (17.4 g, 109 mmol) and phosphorus oxytribromide (47.1 g, 164 mmol) were added to a round-bottom flask. The mixture was heated to 130° C. for several hours. After cooling to rt, the residue was partitioned between saturated Na2CO3 and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (5.x.300 mL). The combined organic layer was washed with H2O (2.x.400 mL) and brine (1.x.400 mL) and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide 4-bromo-2-methylquinoline (8.8 g, 36percent).
16%
With phosphorus tribromide In N,N-dimethyl-formamide at 0 - 20℃; for 3 h;
2-Methylquinolin-4-ol (4.46 g, 28.0 mmol) and N,N-dimethylformamide (80 mL) were added to a 250 mL single-neck flask, then to the mixture in flask was added dropwise phosphorus tribromide (11.37 g, 42 mmol) at 0 °C. After the addition, the reaction mixture was stirred at rt for 3 h. To the reaction mixture was added ice-water (100 mL) and ammonium hydroxide (100 mL, 25percent), then the resulting mixture was extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (ethyl acetate/petroleum ether (v/v) = 1/10) to give the title compound as light yellow liquid (0.995 g, 16percent).MS (ES-API, pos. ion) m/z: 222.9 [M + 2]t
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1865 - 1870
[2] Patent: US2003/229084, 2003, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2017/36404, 2017, A1, . Location in patent: Page/Page column 130
[4] Patent: EP96214, 1991, B1,
[5] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 527 - 536
2
[ 607-67-0 ]
[ 7789-59-5 ]
[ 50488-44-3 ]
Reference：
[1] Patent: US2003/130273, 2003, A1,
3
[ 607-67-0 ]
[ 50488-44-3 ]
[ 500349-69-9 ]
Reference：
[1] Journal of Organic Chemistry, 1947, vol. 12, p. 456,457
0.8 g (5 mmol) of 4-hydroxy-2-methylquinoline, a mixture of 4.87 g (20 mmol) of <strong>[92-55-7](5-nitrofuran-2-yl)methylene diacetate</strong> and 150 ml of acetic anhydride was heated at 150 C for 28 hours, monitored by thin layer chromatography. After the mixture was cooled, concentration in vacuo to remove solvent afforded a crude product, followed by chromatography on an azeotropic column (FC, silica gel, methanol: dichloromethane = 1: 5) (E)-2-(2-(5-nitrofuran-2-yl)ethen-1-yl)quinoline-4-acetic acid methyl ester (Compound 19, 0.73 g, 45% yield).
A solution of 0.8 g (5 mmol) of 4-hydroxy-2-methylquinoline, 4.87 g (20 mmol) <strong>[92-55-7](5-nitrofuran-2-yl)methylene diacetate</strong> and 150 ml of acetic anhydride was heated at 150 C for 30 hours (monitored by thin layer chromatographic). The mixture was cooled and concentrated in vacuo to remove the solvent to obtain a crude product. The crude product was dissolved in pyridine / water (4: 1 by volume) solution at 100 C for 1 hour (monitored by thin layer chromatography). After the mixture was cooled, concentration in vacuo to remove solvent afforded a crude product, chromatographic analysis was performed on an azeotrope tube (FC, silica gel, methanol: dichloromethane = 1: 20)purification, (E)-2-(2-(5-nitrofuran-2-yl)ethen-1-yl)-4-hydroxyquinoline (Compound 21, 0.92 g, 65% yield).
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