反应详情

To a mixture of 7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (1c, 13.0 g, 73.9 mmol) in conc. H2SO4 (120 mL) was added portionwise NCS (10.4 g, 77.6 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured onto ice-water (200 mL). The solution was basified with Na2CO3 (s) to pH 8. The reaction mixture was extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine (300 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 1:1) to give 8-chloro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (1d, 7.8 g, 50%) as a yellow solid.

1. additionThe reaction mixture was poured onto ice-water (200 mL)
2. extractionThe reaction mixture was extracted with EtOAc (2×200 mL)
3. washThe combined organic layers were washed with brine (300 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under vacuum
6. customThe residue was purified by column chromatography (petroleum ether/EtOAc, 1:1)