Water → 1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid

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Reaction Steps

A suspension of 1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester (35.09 g, 0.09 mol) in methanol (0.27 L) and tetrahydrofuran (95.00 mL) was treated with a 3N solution of KOH in water (93.00 mL, 0.28 mol) and stirred at room temperature for 18 hours, then at 45° C. for 2 hours. The organic solvents were evaporated and the residual aqueous slurry diluted with water (0.45 L) and cooled to 0° C. The mixture was set to pH 1 with HCl 3N (85.00 mL) and the precipitated solid was filtered and dried under vacuum. 1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid was obtained as an off-white solid, 34.08 g (100%), MS (ISP): m/e=360.1 (M−H).

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