N-bromobutanimide → 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

Participants

Reaction Steps

293 mg of 5-acetyl-8-benzyloxycarbostyril are dissolved in 15 ml of chloroform, and 200 mg of N-bromosuccinimide are added thereto. The mixture is refluxed for 2 hours under stirring. 300 mg of N-bromosuccinimide are added to the mixture and 4 hours after the commencement of the reaction. 100 mg of N-bromosuccinimide are further added thereto. Six hours after the reaction is started, the mixture is cooled and is allowed to stand at 20° C. for 2 days. Precipitated crystals are collected by filtration. Then, the crystals are washed with methanol and ether and then dried. 110 mg of 5-bromoacetyl-8-benzyloxycarbostyril are thereby obtained as colorless crystals. On the other hand, the filtrate is concentrated to dryness, and the residue is treated in the same manner as above, whereby 60 mg of 5-bromoacetyl-8-benzyloxycarbostyril are further recovered from the filtrate. Total yield: 170 mg (45.8)

Provenance & Evidence