Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([Cl:18])=[C:16]3[C:11]([C:12](=[O:25])[C:13]([C:22]([OH:24])=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:21][CH2:20]3)=[CH:10][C:9]=2[F:26])[CH2:4]1.O.[OH-].[Na+]>CO>[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]([Cl:18])=[C:16]3[C:11]([C:12](=[O:25])[C:13]([C:22]([OH:24])=[O:23])=[CH:14][N:15]3[CH:19]3[CH2:20][CH2:21]3)=[CH:10][C:9]=2[F:26])[CH2:4]1To a 1-liter flask was charged 100 g (0.27 mol) 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid monohydrochloride followed by 200 mL methanol and 200 mL demineralized water. The mixture was stirred and heated to 60° C. where it was maintained until solution was achieved. To a separate 1-liter flask was added 0.5 g Ca(OH)2 and 200 mL demineralized water and the mixture stirred and heated to 60° C. To this mixture was simultaneously added the solution containing the 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid monohydrochloride in aqueous methanol while at the same time charging 5% w/w NaOH at such a rate to maintain the pH between 7.5 and 8.0. When the addition was complete, the mixture was stirred and cooled to 25° C. over 1 hour and filtered on a 4 inch Buchner funnel (filtration time: 38 seconds) and the solid washed with 200 mL demineralized water to give a wet cake. The cake was vacuum dried to give 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as a white solid (90 g).
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