Hydrochloric Acid → Norfloxacin

HRID 2418465Notes

Reaction equation

HRID 2418465 reaction equation
Cl.C([O:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[C:13]([F:18])[CH:14]=2)[N:9]([CH2:25][CH3:26])[CH:8]=1)=[O:6])C>C(O)(=O)C>[CH2:25]([N:9]1[C:10]2[C:15](=[CH:14][C:13]([F:18])=[C:12]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:11]=2)[C:16](=[O:17])[C:7]([C:5]([OH:6])=[O:4])=[CH:8]1)[CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12733941Ethyl norfloxacin

Product 1

HCID 4539NorfloxacinYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of glacial acetic acid (170 ml) and concentrated hydrochloric acid (170 ml) was added 4.3 g of 1-ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester and the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 10 ml of water and adjusted to pH 7.5 with diluted sodium hydroxide solution. The precipitated crystals were carried out by the same way in the Example 1 to give 3.3 g (84% yield) of 1-ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. mp: 220.5°-222° C.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 10 ml of water

Sources & evidence

ORD record
ord-c32462027b574cf4aaca40d0039a8389
Source dataset
uspto-grants-1984_09
Patent number
US04472579

Reaction notes

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