Dichloromethane → 7-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Steps

To the solution of intermediate 17 (7.76 g, 30.4 mmol) in 1,2-dichloroethane (150 mL) was added BF3 (5.52 mL, 48.7 mmol, in MeOH), MsCl (3.8 mL, 48.7 mmol) and TiCl4 (5.35 mL, 48.7 mmol). The mixture was stirred at rt for 5 h. CH2Cl2 (150 mL) was then added to the reaction mixture. The solution was washed with water and brine. The water layer was neutralized by aqueous Na2CO3 to pH=7 and was extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel column (elution with PE/EtOAc=4:1) to give 7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (intermediate 18) (5.1 g, 95%) as a white solid.

Provenance & Evidence