反应详情

A mixture of 1-chloro-3-methyl-4-isoquinoline acetic acid (237 mg., 1.01 mmol) prepared as in Example 8, 4-chlorophenol (260 mg., 2.02 mmol), and potassium tert-butoxide (226 mg., 2.02 mmol) were heated at 100° for 3 hr. After cooling the mixture was diluted with ethyl acetate and water and acidified to pH 1-2. The separated aqueous phase was extracted with 20 ml. ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and vacuum evaporated to a brown oil. Chromatography of this on silica gel eluted with ethyl acetate gave a pale yellow solid; 80 mg., 24%, mp 192°-195° d.

1. temperaturewere heated at 100° for 3 hr
2. temperatureAfter cooling the mixture
3. extractionThe separated aqueous phase was extracted with 20 ml
4. washThe combined organic phases were washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customvacuum evaporated to a brown oil
8. washChromatography of this on silica gel eluted with ethyl acetate
9. customgave a pale yellow solid