Citric Acid → 6-[(2,3-Dichlorophenyl)methyl]-8-fluoro-1-(2-hydroxyethyl)-4-oxo-quinoline-3-carboxylic acid

HRID 491525Notes

Reaction equation

[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[N:11]([CH2:16][CH2:17][OH:18])[CH:10]=[C:9]([C:19]([O:21]CC)=[O:20])[C:8]2=[O:24].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.C1COCC1>[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[N:11]([CH2:16][CH2:17][OH:18])[CH:10]=[C:9]([C:19]([OH:21])=[O:20])[C:8]2=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-8-fluoro-1-(2-hydroxyethyl)-4-oxo-3-quinolinecarboxylate (80 mg, 0.18 mmol) obtained in Step 6 was dissolved in a mixed solvent of ethanol (2 ml) and THF (1 ml), 1N aqueous sodium hydroxide solution (1 ml, 1.0 mmol) was added, and the mixture was stirred with heating at 60° C. for 1 hr. After allowing to cool, 10% aqueous citric acid solution was added to the reaction mixture. The precipitated solid was collected by filtration, washed with 30% aqueous ethanol and vacuum dried to give the object product (70 mg, yield 93%) as a white solid.

Workup

additionwas added
temperatureto cool
filtrationThe precipitated solid was collected by filtration
washwashed with 30% aqueous ethanol and vacuum
customdried

Sources & evidence

ORD record: ord-397ded8f374f41d4bd106753b9032e85
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531554B2

Reaction notes

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