Hydrochloric Acid → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-morpholinocarbonyl-3-hydroxy-3-(2-naphthyl)oxindole

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A mixture of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole (30 mg, 0.0642 mmol), conc. HCl (2 mL), and acetic acid (2 mL) was heated at reflux for 5 h. Excess solvents were azeotropically removed in vacuo by using toluene to give crude carboxylic acid. The residue was dissolved in DMF (0.5 mL) and morpholine hydrochloride (5.6 mg, 0.0453 mmol), 1-hydroxybenzotriazole (7.5 mg, 0.0555 mmol), WSC HCl (8.5 mg, 0.0443 mmol), and triethylamine (0.04 mL, 0.287 mmol) were added. The mixture was stirred for 16 h at room temperature and diluted with sat. aqueous NaHCO3. The mixture was extracted with ethyl acetate-toluene and the extracts were washed with sat. aqueous NaHCO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 30:1 to 25:1 chloroform/methanol to give the title compound (4.8 mg, 18%).

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