4-Chlorobenzoyl chloride → 7-Chloro-3-[(4-chloro-benzoylamino)-methyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

In a 50 mL round-bottomed flask, 3-aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester hydrochloride (intermediate I) (0.30 g, 0.791 mmol) and 4-chlorobenzoyl chloride (138 mg, 0.791 mmol) were added at 0° C. to 15 mL CH2Cl2. The reaction was stirred at 0° C. for 5 min. and then N,N-diisopropylethylamine (511 mg, 3.96 mmol) was added. The reaction mixture was stirred at 0° C. for 1 hr. The mixture was concentrated to dryness and then purified by flash chromatography using 40% ethyl acetate-hexanes. The desired product 7-chloro-3-[(4-chloro-benzoylamino)-methyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (171 mg, 45%) was obtained as a white solid.

Provenance & Evidence