反应详情

温度

150 °C

To a solution of 3,4-dihydrocarbostyril (3 g) in N-methylpyrrolidone (30 ml) are added p-iodobenzoic acid (5.58 g), copper (0.3 g) and potassium carbonate (3.03 g) and the mixture is stirred at 150° C. for 4 hours. An aqueous sodium hydroxide solution is added to the reaction mixture and the mixture is washed with dichloromethane. The aqueous layer is made acidic with concentrated hydrochloric acid and then extracted with diethyl ether and the extract is dried over magnesium sulfate. After the solvent is distilled off under reduced pressure, methanol (50 ml) is added to the residue and thionyl chloride (10 ml) is slowly while to the solution while stirring with ice-cooling. After completion of dropwise addition, the mixture is refluxed for 0.5 hour. After methanol is distilled off under reduced pressure, water is added to the residue and the solution is extracted with dichloromethane and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography to give 1-(4-methoxycarbonylphenyl)-3,4-dihydrocarbostyril (1.44 g).

1. washthe mixture is washed with dichloromethane
2. extractionextracted with diethyl ether
3. dry with materialthe extract is dried over magnesium sulfate
4. distillationAfter the solvent is distilled off under reduced pressure, methanol (50 ml)
5. additionis added to the residue and thionyl chloride (10 ml)
6. stirringwhile stirring with ice-
7. temperaturecooling
8. additionAfter completion of dropwise addition
9. temperaturethe mixture is refluxed for 0.5 hour
10. distillationAfter methanol is distilled off under reduced pressure, water
11. additionis added to the residue
12. extractionthe solution is extracted with dichloromethane
13. dry with materialdried over magnesium sulfate
14. distillationThe solvent is distilled off under reduced pressure
15. customthe resulting residue is purified by silica gel column chromatography