反应详情

A mixture of 6.44 g (0.045 mole) of 1-methylisoquinoline, 6.2 g (0.05 mole) of 3-fluorobenzaldehyde and 18 ml of acetic acid is stirred at a temperature between 130° C. and 140° C. for 3 hours. The termination of the reaction is controlled by thin layer chromatography. The reaction mixture is cooled and 100 ml of anhydrous acetone are added to it. Then it is acidified with a mixture of hydrogen chloride and isopropanol until pH=1 under stirring and cooling with ice-water. The suspension is stirred at a temperature between 0° C. and 5° C. for 2 hours. The separated hydrogen chloride salt is filtered, washed with cold acetone and dissolved in 180 ml of water. To the thus-obtained mixture 20% sodium hydroxide solution is dropped until pH=11-12 under stirring and cooling with ice-water, and the solution is extracted three times with 75 ml each of dichloromethane. The extracts are combined, washed with an aqueous sodium chloride solution, dried over Na2SO4 and evaporated. The crude product is recrystallized from 30 ml of isopropanol. Thus 8.7 g (78%) of 1-(3-fluorostyryl)-isoquinoline are obtained.

1. temperatureThe reaction mixture is cooled
2. stirringunder stirring
3. stirringThe suspension is stirred at a temperature between 0° C. and 5° C. for 2 hours
4. filtrationThe separated hydrogen chloride salt is filtered
5. washwashed with cold acetone
6. dissolutiondissolved in 180 ml of water
7. additionTo the thus-obtained mixture 20% sodium hydroxide solution is dropped until pH=11-12
8. stirringunder stirring
9. temperaturecooling with ice-water
10. extractionthe solution is extracted three times with 75 ml each of dichloromethane
11. washwashed with an aqueous sodium chloride solution
12. dry with materialdried over Na2SO4
13. customevaporated
14. customThe crude product is recrystallized from 30 ml of isopropanol