Norfloxacin → 1-Ethyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 544214Notes

Reaction equation

HRID 544214 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:19])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2].[CH2:24](N(CC)CC)[CH3:25]>CN(C=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:19])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:24][CH3:25])[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4539NorfloxacinHCID 8471Triethylamine

Product 1

HCID 4659311-Ethyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.96 g) (3 millimole), iodoethyl (0.94 g) (6 millimole), triethylamine (0.6 g) (6 millimole) and 10 ml DMF was heated to 70° to 80° C. for 2.5 hours under stirring. After cooling, the reaction mixture was evaporated under vacuum and the residue was dissolved in dichloromethane, washed with water, dried over anhydrous Na2SO4 and the solvent was removed. The residue was recrystallized from a mixture of CHCl3 and benzene to obtain 0.75 g (72%) of 1-ethyl-6-fluoro-7-(4-ethyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid.

Workup

  1. temperaturewas heated to 70° to 80° C. for 2.5 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under vacuum
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. customthe solvent was removed
  8. customThe residue was recrystallized from a mixture of CHCl3 and benzene

Sources & evidence

ORD record
ord-a5e0daca0ec14fb9b7e774b7f7eeeb24
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

Loading…