Lithium Hydroxide → HCID 178427815, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 8-fluoro-4-hydroxy-6-methylquinolone-3-carboxylate (0.50 g) in 30 mL of 1:1 MeOH:THF is added 8 mL of 1M LiOH. The reaction is maintained at 40° C. overnight. The reaction mixture is cooled to room temperature, then diluted with 20 mL glacial acetic acid. The resulting precipitate is collected, washed with H2O, and dried to yield 0.382 g of 8-fluoro-4-hydroxy-6-methyl-3-quinolinecarboxylic acid as a white solid. To a solution of this acid (0.23 g) and 4-chlorophenylhydrazine (0.21 g) in 10 mL DMF is added triethylamine (0.16 m), EDC (0.24 g), and HOBt (0.16 g). The mixture is stirred at room temperature for 3 days. Upon diluting the reaction mixture with 100 mL H2O, an orange solid precipitates. The crude product is adsorbed onto silica and chromatographed eluting with 4% MeOH in CHCl2. Fractions homogenous by TLC are condensed and recrystallized from EtOAc/hexanes to yield 0.0181 g of the desired product as a white solid.

Provenance & Evidence