Sodium Carbonate → 5-bromo-2-(1-propylbutyl)-3,4-dihydroisoquinolin-1(2H)-one

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Reaction Steps

5.8 g of methyl[2-(2-bromophenyl)ethyl](1-propylbutyl)carbamate are dissolved, under an inert atmosphere, in 250 cm3 of dichloromethane, at a temperature close to 20° C. 5.43 g of 4-dimethylaminopyridine are added to the reaction mixture. This is cooled to a temperature close to 0° C. 13 cm3 of trifluoromethanesulfonic anhydride in solution in 250 cm3 of anhydrous dichloromethane are poured into the reaction mixture over 45 min. The suspension is kept stirring for 20 h at a temperature close to 20° C. 300 cm3 of a saturated aqueous solution of sodium carbonate are added to the reaction mixture. The stirring is continued for 30 min. The organic phase is washed with 100 cm3 of a 20% aqueous solution of acetic acid, 100 cm3 of a saturated aqueous solution of sodium carbonate, and 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered through a pellet (50 g) of silica (particle size: 40-63 μm), rinsed with 500 cm3 of dichloromethane and concentrated using a rotary evaporator under reduced pressure (5 kPa). 4.63 g of 5-bromo-2-(1-propylbutyl)-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a yellow oil.

Provenance & Evidence