Hydrochloric Acid → HCID 22716700, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.2 g of 3-(3-bromobenzoyl)-2-ethylamino-6-methylpyridine and 2.1 g of glutaric anhydride was stirred under heating at 150° C. for 15 hours. After cooling to room temperature, 10 ml of 1M hydrochloric acid was added thereto and the whole was heated under reflux for 1 hour. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. To the residue was added 50 ml of ethanol and 0.5 ml of concentrated sulfuric acid, followed by heating under reflux for 1 hour. The reaction mixture was cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The residue was purified by a silica gel column chromatography (chloroform). Thereafter, similar operations to those in Example 2 were carried out to obtain 1.00 g of 3-[4-(3-bromophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid as pale yellow crystals.

Provenance & Evidence