Hydrochloric Acid → HCID 11386597, compound

Participants

Reaction Steps

To a solution of 0.50 g (0.95 mmol) of 4-[4-(5-Chloro-2-methoxy-phenyl)-2-oxo-6-trifluoromethyl-1,2-dihydro-quinolin-3-ylsulfanyl]-benzoic acid ethyl ester in 5 mL of THF and 5 mL of water was added 5.0 mL (5.0 mmol) of 1N NaOH in water. The mixture was stirred for 4 hr, neutralized with 1 N HCl and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated to dryness to afford 0.48 g (100% yield) of the title compound. 1H NMR 400 MHz (DMSOd6) 3.61 (3H, s), 7.19 (4H, m), 7.37 (1H, d, J=2.7 Hz), 7.54 (1H, dd, J=8.8, 2.7 Hz), 7.58 (1H, d, J=8.6 Hz), 7.76 (2H, d, J=8.6 Hz), 7.92 (1H, dd, J=8.8, 1.7 Hz). MS m/z 506 (M+H). HPLC retention time 2.02 min (0% B to 100% B over 2 min at 5 mL/min.; Solvent A=10% MeOH/90% H2O/0.1% TFA, Solvent B=90% MeOH/10% H2O/0.1% TFA; EXTERRA C18 S5 4.6×50 mm column; UV detector at 220 nM).

Provenance & Evidence