Norfloxacin → 1-Ethyl-1,4-dihydro-6-fluoro-4-oxo-7-(4-phthalidyl-1-piperazinyl)quinoline-3-carboxylic acid

HRID 544240Notes

Reaction equation

HRID 544240 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].[OH:24][CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:27](=O)[O:26]1.CN(C)C=O>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]([CH:27]4[C:29]5[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:25](=[O:24])[O:26]4)[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

5

Reactant 3

HCID 4539NorfloxacinHCID 6228DimethylformamideHCID 38042593-Hydroxyisobenzofuran-1(3H)-one

Product 1

HCID 130717601-Ethyl-1,4-dihydro-6-fluoro-4-oxo-7-(4-phthalidyl-1-piperazinyl)quinoline-3-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-ethyl-1,4-dihydro-6-fluoro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid 0.5 g, 3-hydroxyphthalide 0.24 g and dimethylformamide 5 ml was heated at 100°-110° C. for 3 hours under stirring. After cooling, ethanol was added, and the insoluble matters were collected by filtration. The precipitates obtained were washed with ethanol and dried. 0.70 g (99%) of 1-ethyl-1,4-dihydro-6-fluoro-4-oxo-7-(4-phthalidyl-1-piperazinyl)quinoline-3-carboxylic acid was obtained as colorless powders.

Workup

  1. temperaturewas heated at 100°-110° C. for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe insoluble matters were collected by filtration
  4. customThe precipitates obtained
  5. washwere washed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-48c767c4abc241fab72f921bb130eae8
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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