Hydrogen Peroxide → HCID 14221252, compound

Participants

Reaction Steps

To a solution of 5-bromo-2-methyl-8-nitroisoquinolinium tosylate (20.0 g) in CH2Cl2 (400 mL) was added aq. Na2CO3 (5%, 400 mL) and hydrogen peroxide (30%, 20 mL). The resulting mixture was stirred at room temperature for 16 h, the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (5×100 mL). The combined organic layer was washed with water (100 mL), dried over sodium sulfate and evaporated to give the crude product, which was purified by column chromatography on silica gel (EtOAc/CH2Cl2 (1:9)) to give 2.2 g of the desired product (yield: 8%). 1H NMR (CDCl3, 300 MHz): δ=3.60 (s, 3 H), 6.90 (d, J=7.8 Hz, 1 H), 7.28 (d, J=7.2 Hz, 1 H), 7.30 (d, J=7.2 Hz, 1 H), 7.92 (d, J=7.8 Hz, 1 H).

Provenance & Evidence