Diethyl Ether → 5-bromo-2-(2-ethoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Steps

0.363 g of 5-bromo-2-(2-hydroxyethyl)-3,4-dihydroisoquinolin-1(2H)-one is dissolved under an inert atmosphere in 3 cm3 of dimethylsulfoxide at a temperature close to 20° C. 98 mg of finely ground potassium hydroxide are added. The reaction mixture is stirred for 30 min at a temperature close to 20° C., then 0.131 cm3 of iodoethane is introduced. The stirring is continued for 20 h at a temperature close to 20° C. 50 cm3 of a water/ice mixture and 80 cm3 of ethyl ether are added. After decanting, the organic phase is washed with 3 times with 10 cm3 of water, 30 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated using a rotary evaporator under reduced pressure (5 kPa). 356 mg of 5-bromo-2-(2-ethoxyethyl)-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a colorless oil.

Provenance & Evidence