m-Chloroperbenzoic acid → 4-Bromoisoquinoline N-oxide

Participants

Reaction Steps

A solution of 4-bromoisoquinoline (4.16 g, 18.6 mmol) in chloroform (100 mL) was added dropwise over 1 h to a solution of 70% mCPBA (12.4 g, 50.3 mmol) in chloroform (100 mL) at rt. After stirring 18 h, the reaction mixture was washed with 1 N NaOH (2×150 mL), dried (MgSO4) and concentrated under reduced pressure to afford compound 13A (4.23 g, 94%) as an off-white solid. 1H NMR (400 MHz, CDCl3) □8.71 (s, 1H), 8.43 (s, 1H), 8.09 (d, 1H, J=8 Hz), 7.70 (m, 3H).

Provenance & Evidence