反应详情

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%).

1. temperaturewas heated
2. temperatureat reflux for 5 h
3. customExcess solvents were azeotropically removed in vacuo
4. customto give crude carboxylic acid
5. extractionThe mixture was extracted with ethyl acetate-toluene
6. washthe extracts were washed with sat. aqueous NaHCO3
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe residue was purified by silica gel column chromatography with 30:1 to 25:1 chloroform/methanol