Acetic Acid → Oxonorfloxacin

HRID 544221

Reaction equation

HRID 544221 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](Cl)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[O:19]=[C:20]1[CH2:25][NH:24][CH2:23][CH2:22][NH:21]1.N1C=CC=CC=1.C(O)(=O)C>[OH-].[Na+]>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:24]3[CH2:23][CH2:22][NH:21][C:20](=[O:19])[CH2:25]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 231360Piperazin-2-oneHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 130830OxonorfloxacinYield 32.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1-ethyl-7-chloro-1,4-dihydro-6-fluoro-4-oxoquinoline-3-carboxylic acid (0.80 g), 2-oxopiperazine (3.0 g) and 4 ml pyridine was heated for 18 hours. The reaction mixture was evaporated under vacuum, an aqueous solution of caustic soda was added to adjust the pH to 10, ice cooled and the undissolved matter was collected and washed with a small amount of an aqueous solution of NaOH. The filtered product was suspended in water, acidified with acetic acid, filtered and washed. The product obtained was dissolved in an aqueous solution of NaOH and acidified with acetic acid. The precipitate was filtered, washed and dried to obtain 0.32 g (32%) of 1-ethyl-1,4-dihydro-6-fluoro-7-(3-oxo-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid.

Workup

  1. temperaturewas heated for 18 hours
  2. customThe reaction mixture was evaporated under vacuum
  3. additionan aqueous solution of caustic soda was added
  4. temperaturecooled
  5. customthe undissolved matter was collected
  6. washwashed with a small amount of an aqueous solution of NaOH
  7. filtrationfiltered
  8. washwashed
  9. customThe product obtained
  10. filtrationThe precipitate was filtered
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-01db1032b51443d88ced429e4e4f1bed
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Linked notes

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