m-Chloroperbenzoic acid → 6-Methylisoquinoline-2-oxide

Participants

Reaction Steps

To a stirred solution of 6-methylisoquinoline (2.0 g, 14 mmol) in ether (80 mL) at 0° C. was added 3-chloroperbenzoic acid (57%, 4.3 g, 14 mmol). The mixture was warmed to room temperature, stirred for 3 h and filtered. The filter-cake was partitioned between chloroform (3×30 mL) and aqueous potassium carbonate solution (30 mL). The combined organic extracts were washed (brine), dried (sodium sulfate) and concentrated in vacuo to give the product as an off-white crystalline solid (1.2 g, 53%): mp 140-142° C.; IR νmax (Nujol)/cm−1 3047, 2925, 2855, 1606, 1562, 1466, 1377, 1328, 1270, 1217, 1182, 1133, 984, 920, 878, 858, 823, 803, 766, 600, 500 and 498; NMR δH (400 MHz, CDCl3) 2.53 (3H, s) 7.47 (1H, d, J 8.5 Hz) 7.59 (1H, d, .J 7.5 Hz) 7.64 (1H, d, J 8.5 Hz) 8.11 (1H, dd, J 2,7.5 Hz) 8.73 (1H, s).

Provenance & Evidence