Sulfuric Acid → HCID 86723737, compound
Reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[C:15](=[O:17])[NH:14][CH2:13][CH2:12]2.C1C(=O)N([Br:25])C(=O)C1>>[Br:25][C:8]1[C:7]([CH3:6])=[C:16]2[C:11]([CH2:12][CH2:13][NH:14][C:15]2=[O:17])=[CH:10][CH:9]=1Participants
4
Procedure
To cooled conc. H2SO4 (10 mL) was added 8-methyl-3,4-dihydroisoquinolin-1(2H)-one (76b, 1 g, 6.21 mmol) and the reaction mixture was stirred for 10 minutes. NBS (1.1 g, 6.21 mmol) was added and the reaction mixture stirred at 60° C. for 2 hours. The mixture was cooled to room temperature and poured into ice-water (30 mL) with stirring. The suspension was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=1:1) to give 7-bromo-8-methyl-3,4-dihydroisoquinolin-1(2H)-one (76c, 0.63 g, 42%) as a white solid.