Hydrochloric Acid → 7-(4-Acetyl-1-piperazinyl)-1-cyclopropyl-6, 8-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2396985Notes

Reaction equation

HRID 2396985 reaction equation
[N:1]1([C:7]2[C:16]([F:17])=[C:15]3[C:10]([C:11](=[O:24])[C:12]([C:21]([OH:23])=[O:22])=[CH:13][N:14]3[CH:18]3[CH2:20][CH2:19]3)=[C:9]([CH3:25])[C:8]=2[F:26])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].Cl>[OH-].[Na+]>[C:27]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:16]([F:17])=[C:15]3[C:10]([C:11](=[O:24])[C:12]([C:21]([OH:23])=[O:22])=[CH:13][N:14]3[CH:18]3[CH2:19][CH2:20]3)=[C:9]([CH3:25])[C:8]=2[F:26])[CH2:2][CH2:3]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 146511701-Cyclopropyl-6,8-difluoro-1,4-dihydro-5-methyl-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid

Product 1

HCID 146512097-(4-Acetyl-1-piperazinyl)-1-cyclopropyl-6, 8-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 7-(1-piperazinyl)-1-cyclopropyl-6,8-difluoro-5-methyl-1, 4-dihydro-4-oxoquinoline-3carboxylic acid (42 mg) in 5% sodium hydroxide (2 ml) is added acetic anhydride (0.1 ml) at room temperature. After the mixture is made acidic with dilute hydrochloric acid, the resultant is extracted with dichloromethane and the extract is dried over magnesium sulfate. After concentrating, the obtained residue is recrystallized from ethanol to give 7-(4-acetyl-1-piperazinyl)-1-cyclopropyl-6,8-difluoro-5-methyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid (30 mg), as white powder, m.p. 217°-220° C.

Workup

  1. extractionthe resultant is extracted with dichloromethane
  2. dry with materialthe extract is dried over magnesium sulfate
  3. concentrationAfter concentrating
  4. customthe obtained residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-428eefedaf084867951dfa74d1813444
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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