Reaction #792231

Reaction equation

5-hydroxy-3,4-dihydroisoquinolin-1(2H)-one

1-(bromomethyl)-4-[(trifluoromethyl)sulphanyl]benzene

→

5-({4-[(Trifluoromethyl)sulphanyl]benzyl}oxy)-3,4-dihydroisoquinolin-1(2H)-one

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureunder reflux for 6 h
2. 2
   TemperatureAfter cooling
3. 3
   Filtrationthe insoluble constituents were filtered off
4. 4
   Otherthe solvent was removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in chloroform
6. 6
   OtherThe phases were separated
7. 7
   Dryingthe organic phase was dried over sodium sulphate
8. 8
   Otherthe solvent was removed under reduced pressure
9. 9
   OtherThe crude product was purified by chromatography (ethyl acetate:n-heptane 2:1)

Procedure

166 mg (1.017 mmol) of 5-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, 289 mg (1.068 mmol) of 1-(bromomethyl)-4-[(trifluoromethyl)sulphanyl]benzene and 365 mg (2.645 mmol) were suspended in 3 ml of ethanol and stirred under reflux for 6 h. After cooling, the insoluble constituents were filtered off and the solvent was removed under reduced pressure. The residue was dissolved in chloroform and water. The phases were separated, the organic phase was dried over sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified by chromatography (ethyl acetate:n-heptane 2:1). This gave 200 mg (54% of theory) of the desired 5-({4-[(trifluoromethyl)sulphanyl]benzyl}oxy)-3,4-dihydroisoquinolin-1(2H)-one. 1H-NMR (400 MHz, d6-DMSO δ, ppm) 7.89 (br. s, 1H), 7.52-7.44 (m, 4H), 7.28 (t, 1H), 7.22 (d, 1H), 5.16 (s, 2H), 3.33 (dt, 2H), 2.84 (t, 2H).

Source