反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
To a solution of 5-(3,5-dichloro-phenyl)-3-(3-nitro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (15.0 g, 37 mmol) (Example I2) in isopropanol (120 ml) was added tin(II) chloride (25 g, 133 mmol). The mixture was cooled to 0° C. and aqueous hydrochloric acid (concentrated) (23 ml) was added slowly at 0° C. The reaction mixture was heated to 80° C. for 2 hours. Then ⅓ of the total volume of isopropanol was evaporated. Water (100 ml) was added to the mixture and aqueous sodium hydroxide (4N) was added to adjust the pH to 8-9. The aqueous phase was extracted three times with ethyl acetate (200 ml). The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1) to give 3-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenylamine (8.1 g, 58% yield). 1H-NMR (CDCl3, 400 MHz): 7.56 (m, 2H), 7.43 (m, 1H), 7.20 (t, 1H), 7.05 (m, 1H), 6.97 (m, 1H), 6.78 (m, 1H), 4.08 (d, 1H), 3.8 (s, 1H), 3.68 (d, 1H).
WORKUP
后处理
- temperatureThe reaction mixture was heated to 80° C. for 2 hours
- customThen ⅓ of the total volume of isopropanol was evaporated
- additionWater (100 ml) was added to the mixture and aqueous sodium hydroxide (4N)
- additionwas added
- extractionThe aqueous phase was extracted three times with ethyl acetate (200 ml)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1)