N-bromobutanimide → 1-Bromo-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (103 mg, 0.35 mmol), N-bromosuccinimide (65 mg, 0.37 mmol), benzoyl peroxide (4.2 mg, 0.02 mmol), and carbon tetrachloride (2.5 mL) was refluxed for 4 h before it was cooled to room temperature and filtered. The filtrate was washed with water, saturated aqueous sodium bicarbonate solution, and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (128 mg): MS: (+) m/z 374.0, 376.0 (M+1, 79Br/81Br), MS: (−) m/z 372.1, 374.1 (M−1, 79Br/81Br).

Provenance & Evidence