5-bromo-3,4-dihydro-2H-isoquinolin-1-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.15 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one in 5 cm3 of dimethylformamide is poured into a mixture containing 31 mg of sodium hydride (60% in oil) and 10 cm3 of dimethylformamide at a temperature close to 20° C. under an inert atmosphere. Then a solution of 0.2 g of 1-(1-bromoethyl)-4-fluorobenzene in 5 cm3 of dimethylformamide is poured into the reaction mixture. The latter is stirred for 20 h at a temperature close to 20° C. Water and ethyl acetate are added to the reaction mixture. After decanting, the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The 325 mg of crude product obtained are purified by filtration through a silica pellet (eluent: 20% ethyl acetate/80% cyclohexane). After concentrating the fractions under reduced pressure, 146 mg of 5-bromo-2-[1-(4-fluorophenyl)ethyl]-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a thick pale yellow oil. close to 20° C. under an inert atmosphere close to 20° C After decanting the organic phase is washed with a saturated aqueous solution of sodium chloride dried over magnesium sulfate filtered then concentrated a rotary evaporator under reduced pressure (5 kPa)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.36 g of methyl[2-(2-bromophenyl)ethyl]carbamate and 5.2 g of phosphoric acid are stirred under an inert atmosphere at a temperature close to 150° C. The reaction mixture is cooled to a temperature close to 20° C., then it is hydrolysed with a mixture of water and ethyl acetate using ultrasound treatment. After decanting, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water, a saturated aqueous solution of sodium chloride, then concentrated using a rotary evaporator under reduced pressure (5 kPa). 0.105 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one is obtained in the form of an amorphous beige solid. close to 150° C The reaction mixture is cooled to a temperature close to 20° C. After decanting the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water a saturated aqueous solution of sodium chloride, then concentrated a rotary evaporator under reduced pressure (5 kPa)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.15 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one in 5 cm3 of dimethylformamide is poured into a mixture containing 31 mg of sodium hydride (60% in oil) and 10 cm3 of dimethylformamide at a temperature close to 20° C. under an inert atmosphere. Then a solution of 0.2 g of 1-(1-bromoethyl)-4-fluorobenzene in 5 cm3 of dimethylformamide is poured into the reaction mixture. The latter is stirred for 20 h at a temperature close to 20° C. Water and ethyl acetate are added to the reaction mixture. After decanting, the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The 325 mg of crude product obtained are purified by filtration through a silica pellet (eluent: 20% ethyl acetate/80% cyclohexane). After concentrating the fractions under reduced pressure, 146 mg of 5-bromo-2-[1-(4-fluorophenyl)ethyl]-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a thick pale yellow oil. close to 20° C. under an inert atmosphere close to 20° C After decanting the organic phase is washed with a saturated aqueous solution of sodium chloride dried over magnesium sulfate filtered then concentrated a rotary evaporator under reduced pressure (5 kPa)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.36 g of methyl[2-(2-bromophenyl)ethyl]carbamate and 5.2 g of phosphoric acid are stirred under an inert atmosphere at a temperature close to 150° C. The reaction mixture is cooled to a temperature close to 20° C., then it is hydrolysed with a mixture of water and ethyl acetate using ultrasound treatment. After decanting, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water, a saturated aqueous solution of sodium chloride, then concentrated using a rotary evaporator under reduced pressure (5 kPa). 0.105 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one is obtained in the form of an amorphous beige solid. close to 150° C The reaction mixture is cooled to a temperature close to 20° C. After decanting the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water a saturated aqueous solution of sodium chloride, then concentrated a rotary evaporator under reduced pressure (5 kPa)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.36 g of methyl[2-(2-bromophenyl)ethyl]carbamate and 5.2 g of phosphoric acid are stirred under an inert atmosphere at a temperature close to 150° C. The reaction mixture is cooled to a temperature close to 20° C., then it is hydrolysed with a mixture of water and ethyl acetate using ultrasound treatment. After decanting, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water, a saturated aqueous solution of sodium chloride, then concentrated using a rotary evaporator under reduced pressure (5 kPa). 0.105 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one is obtained in the form of an amorphous beige solid. close to 150° C The reaction mixture is cooled to a temperature close to 20° C. After decanting the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water a saturated aqueous solution of sodium chloride, then concentrated a rotary evaporator under reduced pressure (5 kPa)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.15 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one in 5 cm3 of dimethylformamide is poured into a mixture containing 31 mg of sodium hydride (60% in oil) and 10 cm3 of dimethylformamide at a temperature close to 20° C. under an inert atmosphere. Then a solution of 0.2 g of 1-(1-bromoethyl)-4-fluorobenzene in 5 cm3 of dimethylformamide is poured into the reaction mixture. The latter is stirred for 20 h at a temperature close to 20° C. Water and ethyl acetate are added to the reaction mixture. After decanting, the organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). The 325 mg of crude product obtained are purified by filtration through a silica pellet (eluent: 20% ethyl acetate/80% cyclohexane). After concentrating the fractions under reduced pressure, 146 mg of 5-bromo-2-[1-(4-fluorophenyl)ethyl]-3,4-dihydroisoquinolin-1(2H)-one are obtained in the form of a thick pale yellow oil. close to 20° C. under an inert atmosphere close to 20° C After decanting the organic phase is washed with a saturated aqueous solution of sodium chloride dried over magnesium sulfate filtered then concentrated a rotary evaporator under reduced pressure (5 kPa)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.36 g of methyl[2-(2-bromophenyl)ethyl]carbamate and 5.2 g of phosphoric acid are stirred under an inert atmosphere at a temperature close to 150° C. The reaction mixture is cooled to a temperature close to 20° C., then it is hydrolysed with a mixture of water and ethyl acetate using ultrasound treatment. After decanting, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water, a saturated aqueous solution of sodium chloride, then concentrated using a rotary evaporator under reduced pressure (5 kPa). 0.105 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one is obtained in the form of an amorphous beige solid. close to 150° C The reaction mixture is cooled to a temperature close to 20° C. After decanting the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water a saturated aqueous solution of sodium chloride, then concentrated a rotary evaporator under reduced pressure (5 kPa)