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4-Amino-2-fluorobenzoic acid (E-1,1.0 g, 6.4 mmol), glycerin (2.1 g, 28.7 mmol) and sodium3-nitrobenzenesulfonate (2.9 g, 12.8 mmol) were added to the mixture of H2SO4(12 ml) and water (4 ml). The mixture was heated at 120C for 4 h. After cooledto 60C, EtOH (25 ml) was added to the reaction and stirred at 60C for 3 d.The mixture was cooled to rt and poured to a large amount of ice water,saturated Na2CO3 aqueous was added to adjust to pH=8,then extracted with EtOAc, washed with brine and dried over anhydrous Na2SO4,then the residue was purified by flash column chromatography to afford themixture of ethyl 7-fluoroquinoline-6-carboxylate (E-2) and ethyl 5-fluoroquinoline-6-carboxylate (F-1) as yellow solid (1.0 g, 71% yield).LC-MS (ESI): [M+H]+=220. The mixture of E-2 and F-1 (1.0 g, 4.6 mmol)were dissolved in the solution of EtOH (18 ml) and H2O (5 ml), thenLiOH·H2O (0.6 g, 14.3 mmol) was added slowly at 0C. The mixture wasstirred at rt overnight. After removal of EtOH, 6N HCl was added to adjust topH=5, then filtrated, washed with water and dried, the mixture of 7-fluoroquinoline-6-carboxylicacid (E-3) and 5-fluoroquinoline-6-carboxylicacid (F-2) was obtained as palewhite solid (0.6 g, 70% yield). LC-MS (ESI): [M+H]+=192.
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