8-Fluorociprofloxacin → 1-Cyclopropyl-8-ethoxy-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

HRID 2249259Notes

Reaction equation

HRID 2249259 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:26])=[C:16]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:17]=3F)[C:12](=[O:27])[C:11]([C:28]([OH:30])=[O:29])=[CH:10]2)[CH2:8][CH2:7]1>C(O)C>[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:26])=[C:16]([N:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)[C:17]=3[O:1][CH2:2][CH3:3])[C:12](=[O:27])[C:11]([C:28]([OH:30])=[O:29])=[CH:10]2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 1228488-FluorociprofloxacinHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 4845751-Cyclopropyl-8-ethoxy-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide prepare from sodium (0.75 g) and absolute ethanol (30 ml) was added 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid (0.8 g) and the mixture in sealed tube was stirred for 52 hours at 140° to 150° C. and then concentrated. Water (60 ml) was added to the residue, and the solution was adjusted pH 7 with acetic acid and extracted with chloroform. The chloroform layer was washed with saturated saline solution, dried over anhydrous sodium sulfate and then concentrated. The resulting residue was purified by silica gel column chromatography eluting with chloroform-methanol (2:1) → chloroform-methanol-concentrated aqueous ammonia (20:6:1 → 10:10:1) and recrystallized from ethanol to give the title compound (75 mg) as light brown prisms, mp 119°-122° C.

Workup

  1. concentrationconcentrated
  2. additionWater (60 ml) was added to the residue
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography
  8. washeluting with chloroform-methanol (2:1) → chloroform-methanol-concentrated aqueous ammonia (20:6:1 → 10:10:1)
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-367b97c7849945dab5ad2367bf92e518
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Reaction notes

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