Dimethylformamide → 1,2-Dihydro-2-oxo-6-[(5-oxo-2-pyrrolidinyl)amino]3-quinolinecarboxylic acid

Participants

Reaction Steps

A mixture of 2.32 g (18 mmol) 5-oxo-L-proline, 1.39 ml (18 mmol) dimethylformamide, and 45 ml of dichloromethane is stirred at 0°-5° and 1.32 ml (18 mmol) of thionyl chloride is added. The reaction mixture is stirred at 0°-5° for 1 hour. A mixture of 2.45 g (12 mmol) of 6-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 100 ml of dichloromethane, 5.04 ml (36 mmol) triethylamine and 4.57 ml (36 mmol) chlorotrimethylsilane is stirred at room temperature for 40 min and then is cooled to 0°-5°. The solution of the acid chloride complex is added to the silylated quinoline acid and is stirred with cooling for 4 hours and at room temperature overnight. The reaction mixture is evaporated to dryness, and the residue is treated with methanol and filtered to give 2.1 g of 1,2-dihydro-2-oxo-6-[(5-oxo-2-pyrrolidinyl)amino]3-quinolinecarboxylic acid. mp>300°

Provenance & Evidence