Boron tribromide → 9-Hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

Participants

Reaction Steps

To a suspension of 9-methoxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one (0.048 g, 0.21 mmol) and CH2Cl2 (2 ml) was added boron tribromide (1.05 ml of 1M sol. in CH2Cl2, 1.05 mmol), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was evaporated, methanol (2 ml) was added, the resulting mixture stirred for 1 hour and then evaporated. The resulting solid was purified by flash chromatography on SiO2 gel to yield the title compound (0.042 g, a 90% yield) as a solid. m.p.>250° C.; 1H NMR (400 MHz, DMSO) δ 7.28 (d, 1H, Ar), 7.47 (t, 1H, Ar), 7.75 (d, 1H, Ar), 9.06 (s, 1H, 2-CH), 10.36 (s, 1H, OH), 12.41 (s, 1H, NH).

Provenance & Evidence