Methanesulfonic Acid → 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Participants

Reaction Steps

NaN3 (6.2 g, 94.78 mmol) was added to a solution of 5-bromo-1-indanone (10 g, 47.39 mmol) in 40 mL of mixture of methane sulphonic acid and dichloromethane (1:1) in portion wise at 0° C.-5° C. The resulting mixture was stirred for 8 h at room temperature. The reaction mixture was cooled to 0° C. in ice bath, neutralized with 5% aq. NaOH, and aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with water and brine solution, dried over Na2SO4 and filtered. The filtrate was concentrated under vacuum and purified by silica gel flash column chromatography using 30% ethyl acetate in hexane to afford title compound (6.4 g, 60%) as solid. 1H NMR (400 MHz, CDCl3): δ 7.95 (d, J=8.4 Hz, 1H), 7.5 (d, J=8.4 Hz, 1H), 7.4 (s, 1H), 6.1 (bs, 1H), 3.6 (t, J=6.8 Hz, 2H), 3 (t, J=6.4 Hz, 2H).

Provenance & Evidence