Acetic Acid → 3-Quinolinecarboxylic acid, 7-(4-acetyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-

HRID 544241Notes

Reaction equation

HRID 544241 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].O.[C:25](O)(=[O:27])[CH3:26]>>[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]([C:25](=[O:27])[CH3:26])[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 3

HCID 176Acetic Acid2×HCID 962WaterHCID 4539Norfloxacin

Product 1

HCID 1562683-Quinolinecarboxylic acid, 7-(4-acetyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-Yield 97%

Procedure

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid 3.2 g was dissolved in 20 ml of glacial acetic acid, 2.0 g of anhydrous acetic acid was added thereto and the mixture was heated at 90°-100° C. for 2 hours with stirring. After cooling, 50 ml of water was added thereto. The precipitated crystals were collected by filtration, washed and dried. The crystals were recrystallized from dimethylformamide to obtain 3.5 g (97%) of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-acetyl-1-piperazinyl)quinoline-3-carboxylic acid as colorless needles.

Workup

  1. temperaturethe mixture was heated at 90°-100° C. for 2 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed
  5. customdried
  6. customThe crystals were recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-2b98e1b0bdd7483bba6098c56563c407
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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