N-bromobutanimide → 4-Quinolinecarboxylic acid, 3-(bromomethyl)-2-phenyl-, methyl ester

Participants

Reaction Steps

10 g (36 mmol) of 3-methyl-2-phenylquinoline-4-carboxylic acid methyl ester (compound of Description A) were dissolved in 500 ml of CH3CN; 13 g (72 mmol) of N-bromosuccinimide were added and the reaction mixture was heated to reflux. After adding 1 g (4.1 mmol) of dibenzoylperoxide, the reaction was refluxed for 24 h; then additional 4 g (22.5 mmol) of N-bromosuccinimide and 0.5 g (2.0 mmol) of dibenzoylperoxide were added and the reaction was refluxed for 4 h. The solvent was evaporated in vacuo to dryness to yield 26.1 g of crude methyl 3-bromomethyl-2-phenylquinoline-4-carboxylate (theorical amount, 12.8 g) which was used in the following reaction without further purification.

Provenance & Evidence