Water → 8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Steps

To a 0° C. solution of 8-chloro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (1d, 7.8 g, 3.7 mmol) in dry CH2Cl2 (120 mL) was added dropwise BBr3 (11 mL, 111 mmol). After the addition, the mixture was stirred at room temperature overnight. To the reaction mixture was added dropwise H2O (200 mL). The mixture was extracted with EtOAc (8×200 mL), dried over Na2SO4 and concentrated under vacuum. To the residue was added EtOAc (20 mL) and petroleum ether (40 mL). The mixture was filtered and the solids were dried under vacuum to give 8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (1e, 6.6 g, 91%) as a brown solid.

Provenance & Evidence