Carbon Dioxide → 1-Cyclopropyl-6-fluoro-8-methyl-7-(isoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
Reaction equation
Br.[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:25])=[C:12]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[CH2:21][NH:20][CH2:19]5)[C:13]=3[CH3:15])[C:8](=[O:26])[C:7]([C:27]([OH:29])=[O:28])=[CH:6]2)[CH2:4][CH2:3]1.C(=O)=O>C(O)C.[OH-].[Na+]>[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:25])=[C:12]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[CH2:21][NH:20][CH2:19]5)[C:13]=3[CH3:15])[C:8](=[O:26])[C:7]([C:27]([OH:29])=[O:28])=[CH:6]2)[CH2:3][CH2:4]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
In 5.3 ml of 47% hydrobromic acid was suspended 0.53 g of 1-cyclopropyl-6-fluoro-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3 carboxylic acid, and 0.28 g of phenol and 3.2 ml of propionic acid were added to the suspension, after which the resulting mixture was heated under reflux for one hour under a nitrogen stream. The reaction mixture was concentrated under reduced pressure, and ethanol was added to the residue obtained, after which the crystals formed were collected by filtration, to obtain 0.38 g of colorless, crystalline 1-cyclopropyl-6-fluoro-8-methyl-7-(isoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrobromide. The hydrobromide obtained was suspended in 3.8 ml of ethanol and then dissolved in 7.6 ml of 0.5N aqueous sodium hydroxide solution, after which a carbon dioxide gas was blown into the solution. The crystals formed were collected by filtration, to obtain 0.27 g of colorless, crystalline 1-cyclopropyl-6-fluoro-8-methyl-7-(isoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.
Workup
- customThe crystals formed
- filtrationwere collected by filtration
Sources & evidence
- ORD record
- ord-a23b9f7ebca74a0c9fe1b49430c05eda
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05935952
Reaction notes
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