Ammonia → 4-Quinolone-3-carboxylic acid
Reaction equation
C1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10](F)=[C:11](N4C[C@H](C)N[C@H](C)C4)[CH:12]=3)[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)CC1.N>>[O:24]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][CH:5]=[C:6]1[C:25]([OH:27])=[O:26]Participants
Procedure
In a sealed tube, 1-cyclopropyl-5,6-difluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 28% aqueous ammonia were heated at 100° C. for 48 hours. The reaction mixture was concentrated under reduced pressure. A 1N aqueous solution of sodium hydroxide was added to the residue, and the insoluble matter was removed by filtration. A 10% aqueous solution of acetic acid was added to the filtrate to adjust its pH to 8, and it was then extracted with chloroform. The extract was dried and concentrated. Acetonitrile was added to the residue, and the mixture was cooled with ice. The crystals were collected by filtration and recrystallized from aqueous ammonia to give 5-amino-1-cyclopropyl-6-fluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid m p. 253°-254° C.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionA 1N aqueous solution of sodium hydroxide was added to the residue
- customthe insoluble matter was removed by filtration
- additionA 10% aqueous solution of acetic acid was added to the filtrate
- extractionwas then extracted with chloroform
- customThe extract was dried
- concentrationconcentrated
- additionAcetonitrile was added to the residue
- temperaturethe mixture was cooled with ice
- filtrationThe crystals were collected by filtration
- customrecrystallized from aqueous ammonia
Sources & evidence
- ORD record
- ord-8b2393fe83cc4d5ab8ecaaeccdb5f714
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05164392
Reaction notes
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