Hydrochloric Acid → HCID 86732836, compound

Participants

Reaction Conditions

Reaction Steps

To a pale brown suspension of 5-amino-1-cyclopropyl-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (9 g, 29.6 mmol) in con. HCl (60 mL) stirred at 0° C. was added dropwise a cold solution of sodium nitrite (2.143 g, 31.1 mmol) in Water (20.00 mL). Stirring continued at 0° C. for 1 h. LCMS indicated completion of reaction. HCl (80 mL, 2633 mmol) was added and the mixture was heated at 95° C. for 6 h. LCMS indicated completion of reaction. The reaction mixture was cooled down to rt and then poured into water. The precipitates were collected by filtration and dried to afford 5-chloro-1-cyclopropyl-6-hydroxy-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7.4 g, 23.89 mmol, 81% yield) as a pale yellow solid. LCMS: [M+H]+: 310.1.

Provenance & Evidence