Potassium Hydroxide → 2-Chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid

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Reaction Steps

3 M Potassium hydroxide solution (2 ml) was added to a solution of crude 2-chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid methyl ester (0.097 g, 0.13 mmol) in MeOH (2 ml) and tetrahydrofuran (1 ml) and the mixture stirred for 16 hours. The organic solvent was evaporated and the solution neutralized with 3 M HCl solution (3 ml) forming a white precipitate. The precipitate was filtered and washed with heptane. The solid was then dried under vacuum to give 2-chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid, 0.037 g, as a red solid. LC @215 nm; Rt 2.06: 98%, m/z (ES+): 489.23 (M+H+.); δH (400 MHz; d6-DMSO) 13.18 (1H, br.s), 10.63 (1H, s), 8.22 (1H, d), 8.08 (1H, d), 7.83-7.91 (2H, m), 7.76 (1H, dd), 7.55-7.67 (2H, m), 7.43-7.48 (2H, m), 7.30 (1H, d), 3.84 (2H, m), 2.52 (2H, m), 1.62 (2H, m).

Provenance & Evidence