Lithium Hydroxide → 3-(4-Carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 7-chloro-3-(4-methoxycarbonyl-benzyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (compound 10, 31 mg) and LiOH (1 M aq, 1 mL) in MeOH (10 mL) was stirred at RT overnight. The reaction mixture was then stirred at 50° C. for 3 h, then extracted with EtOAc. The organic layer was separated, the aqueous layer acidified by adding AcOH (aq), and the resulting mixture extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by preparative TLC (hexane/acetone, 70:30+1% AcOH) to afford 11 mg of 3-(4-carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester as an off-white solid. MS=447; MP=258.0-261.0° C.

Provenance & Evidence