Sodium Dithionite → 2,7-Dichloro-6-fluoroquinoline-3-carboxylic acid

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Reaction Steps

A solution of potassium permanganate (89.3 g) in water (1.4 liters) is added in the course of 1 hour to a stirred suspension, cooled to 10° C., of 2,7-dichloro-6-fluoro-3-formyl-1,4-dihydroquinoline (69.5 g) in 2 N aqueous potassium hydroxide (282 cc) and water (282 cc) while the temperature is maintained at between 10° and 14° C. The temperature is allowed to rise to approximately 20° C. and the mixture is stirred for a further 30 minutes at this temperature. Sodium dithionite (26 g) is added and the mixture is stirred for 10 minutes at a temperature in the region of 20° C., filtered through diatomaceous silica for filtration and washed with water (2×250 cc). The filtrate and the aqueous washing phases are combined and treated with 35% strength aqueous hydrochloric acid solution (90 cc). The precipitate formed is extracted with ethyl acetate (4×500 cc). The combined organic extracts are washed with water (3×500 cc), dried over magnesium sulphate, filtered and concentrated under reduced pressure (20 kPa) at 50° C. The residue is taken up with ethyl ether (350 cc), drained and washed with ethyl ether (2×200 cc). 2,7-Dichloro-6-fluoro-3-quinolinecarboxylic acid (45 g) is obtained in the form of a beige solid, m.p. 230° C., which is used without further purification for the subsequent steps.

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