Reaction #985292
ord-ad37b714cf6b4a51939c308075b4d8e7
Reaction equation
Reactants
Reagents
Solvents
Conditions
Workup
- 1Temperaturecooled at room temperature
- 2workup.STIRRINGThe reaction mixture was stirred at room temperature for 2 h
- 3Temperaturecooled at 0-5° C.
- 4workup.STIRRINGstirred for 1 h
- 5OtherThe precipitate obtained
- 6Filtrationwas filtered
- 7Washwashed with cold water, cold EtOH
- 8Otherdried at 110° C. under reduced pressure for 1 h
- 9workup.ADDITIONThe crude product was treated with HCl (6% aqueous solution)
- 10Temperatureheating for 1 h in the presence of charcoal
- 11FiltrationAfter filtration
- 12Temperaturethe solution was cooled to 35-40° C.
- 13Othera first precipitation
- 14FiltrationThe precipitate was filtered
- 15Washwashed with water
- 16Otherdried at 110° C. for 1 h
Procedure
7-Chloro-1-cyclopropyl-1,4-dihydro-6-fluoro4-oxo-quinoline-3-carboxylic acid (56.3 g) and ethylenediamine (36 g) were dissolved in N,N-dimethylacetamide (650 mL) at 100° C. and stirred for 8.5 h at 115° C. Water (700 mL) was added to the reaction mixture cooled at room temperature. The reaction mixture was stirred at room temperature for 2 h, cooled at 0-5° C. and stirred for 1 h. The precipitate obtained was filtered, washed with cold water, cold EtOH, and dried at 110° C. under reduced pressure for 1 h. The crude product was treated with HCl (6% aqueous solution) heating for 1 h in the presence of charcoal. After filtration, the solution was cooled to 35-40° C. and a first precipitation happened. The precipitate was filtered, washed with water and dried at 110° C. for 1 h. The title compound (6.4 g) was obtained as the hydrochloride salt. The hydrochloride salt was then converted to the free base using standard conditions.