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A solution of 3: 1 concentrated sulfuric acid/concentrated nitric acid (32 ml) was added dropwise to 3-fluoroquinoline (13.04 g, 88.6 mmol) in concentrated sulfuric acid (100 ml) at 00C. After stirring for 2 h, the solution was made alkaline with IO N aq. NaOH and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 3-fluoro-8-nitroquinoline and 3-fluoro- 5-nitroquinoline as a yellow solid. Method [7] retention time 3.50 and 3.92 min by HPLC (M+ 193) and (M+ 193).3-Fluoro-8-nitroquinoline, 3-fluoro-5-nitroquinoline, and tin(II)chloride- dihydrate (68.23 g, 302 mmol) in ethyl acetate (200 ml) was placed into a preheated oil bath at 600C. After heating for 4 h, the solution was cooled to ambient temperature, diluted with 3 N aq. NaOH, and filtered through a pad of celite. The filtrate was extracted with ethyl acetate, the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 19: 1, 9: 1, 17:3, 4: 1, 3: 1, 7:3, and 3:2 hexane:ethyl acetate as the eluant to afford 2.14 g (11% yield over two steps) 3- fluoroquinolin-8-amine and 7.02 g (37% yield over two steps) of 3-fluoroquinolin-5-amine. Method [6] retention time 1.57 and 4.02 min by HPLC (M+ 163) and (M+ 163).
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