Phosphorus oxybromide → HCID 89813158, compound

Participants

Reaction Steps

A mixture of butyl 1,4-dihydroxy-6-(o-tolyloxy)isoquinoline-3-carboxylate (1.5 g, 4.2 mmol) and POBr3 (4.9 g, 16.8 mmol) in acetonitrile (32 mL) was heated to reflux for 90 minutes. After cooling to room temperature, the solvent was removed in vacuo. The residue was dissolved in CHCl3 (200 mL) and to the solution were added NaHCO3 (10 g) and H2O (13 mL). The resulting mixture was stirred vigorously at room temperature for 30 minutes before dried over MgSO4. The mixture was then filtered and the filtrate was concentrated in vacuo and then purified by flash chromatography (0-10% EtOAc/CH2Cl2) to give the title compound in 0.9 g. 1H NMR (CDCl3, 200 MHz): δ=11.74 (s, 1H), 8.21 (d, 1H, J=8.4 Hz), 7.52-7.44 (m, 2H), 7.34-7.15 (m, 3H), 7.03 (d, 1H, J=8.8 Hz), 4.46 (t, 2H, J=7.2 Hz)), 2.20 (s, 3H), 1.92-1.77 (m, 2H), 1.56-1.38 (m, 2H), 0.98 (t, 3H, J=7.2 Hz).

Provenance & Evidence