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Hydrochloric Acid → 1-Cyclopropyl-7-(4-acetyl-3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1638692
Notes
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Reaction equation

HRID 1638692 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([N:15]4[CH2:20][CH2:19][NH:18][CH:17]([CH3:21])[CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].Cl>[OH-].[Na+]>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([N:15]4[CH2:20][CH2:19][N:18]([C:27](=[O:29])[CH3:28])[CH:17]([CH3:21])[CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 140525871-Cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 156225161-Cyclopropyl-7-(4-acetyl-3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798
Sodium Hydroxide
Solvent

Procedure

1-Cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.3 g) is dissolved in 10% aqueous sodium hydroxide (5 ml), and thereto is added acetic anhydride (0.3 ml) at room temperature, and the mixture is stirred at the same temperature for 30 minutes. The reaction mixture is acidified with conc. hydrochloric acid and is extracted with dichloromethane. After removing the solvent by concentration, the resulting residue is purified by silica gel column chromatography (solvent, dichoromethane) and then recrystallized from methanol to give 1-cyclopropyl-7-(4-acetyl-3-methyl-1-piperazinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.1 g), as white powder, m.p. 219°-221° C.

Workup

  1. extractionis extracted with dichloromethane
  2. customAfter removing the solvent
  3. concentrationby concentration
  4. customthe resulting residue is purified by silica gel column chromatography (solvent, dichoromethane)
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-caa7df7ca94c419c9f2bde56a81b55a1
Source dataset
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04880806

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes