Hydrogen Bromide → 7-Bromo-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-amino-3,4-dihydro-1(2H)-isoquinolinone, (for a synthesis see Girard, Yves; Atkinson, Joseph G.; Belanger, Patrice C.; Fuentes, Jose J.; Rokach, Joshua; Rooney, C. Stanley; Remy, David C.; Hunt, Cecilia A J. Org. Chem. (1983), 48(19), 3220) (0.773 g, 4.772 mmol) in acetonitrile (10 ml) at 0° C. was added 48% aqueous hydrobromic acid (10 ml, precooled to 0° C.). The mixture was stirred at 0° C. for 0.5 h before addition of a solution of sodium nitrite (0.379 g, 5.49 mmol) in water (2 ml) over 0.4 h. The reaction was then stirred at 0° C. for 0.5 h and then copper(I) bromide (0.822 g, 5.726 mmol) was added portionwise over 10 min. The reaction mixture was then warmed to room temperature, stirred at room temperature for 0.5 h and then at 70° C. for 1 h. The reaction mixture was then cooled to 0° C., water (60 ml) was added and the mixture stirred at 0° C. for 1 h before filtering and drying in vacuo. The residue was dissolved in 10% methanol/dichloromethane, dried with magnesium sulphate and evaporated to give the desired product (0.679 g, 63%).

Provenance & Evidence