(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester → (5-Fluoro-quinolin-6-yl)-acetic acid methyl ester

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Reaction Steps

(5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester (5 g, 19 mmol) in 25 ml of aq. NaOH (4N) was heated to reflux for 4 h. The mixture was washed with ethyl acetate and the aqueous layer was acidified to pH 5 with conc. HCl. The resulting precipitate was collected and washed with water and dried in vacuo to return (5-fluoro-quinolin-6-yl)-acetic acid. To this solid was added conc.H2SO4 (1.2 ml) and MeOH (20 ml) and the solution heated to reflux for 6 h. After cooling the solvent was removed in vacuo and the residue purified by flash column chromatography to return the title compound (2.0 g 48%).

Provenance & Evidence