Sodium Azide → HCID 117780509, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 158f (650 mg, 3 mmol) in dichloromethane (6 mL) and methanesulfonic acid (3 mL) was added sodium azide (0.293 mg, 4.5 mmol). See FIG. 4. The reaction mixture was stirred at 20° C. for 16 h. The reaction mixture was partitioned between DCM (50 mL) and aqueous sodium hydroxide solution (50 mL, 1.0 M). The aqueous layer was extracted with DCM (20 mL×3). The combined organic layers were washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:petroleum ether=1:2) to give 6-(trifluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one 158g (340 mg, 49%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.21 (br s, 1H), 7.20 (s, 1H), 7.13 (d, J=8.8 Hz, 1H), 6.89 (d, J=8.8 Hz, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.48-2.31 (m, 2H)

Provenance & Evidence