Sodium Hydroxide → 8-iodo-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Steps

To a mixture of 7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (53a, 1.7 g, 9.6 mmol) in conc. H2SO4 (40 mL) was added portionwise NIS (2.4 g, 11 mmol) at 0° C. The mixture was stirred at room temperature for 14 hours. The mixture was chilled to 0° C. and basified with aq. NaOH to pH 8. The mixture was extracted with EtOAc (5×60 mL). The combined organic layers were washed with brine (3×60 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 1:1) to give 8-iodo-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (53b, 2.1 g, 79%) as a yellow solid.

Provenance & Evidence