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

HRID 544214노트

반응식

HRID 544214 반응식
[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]

참가 물질

4

반응물 2

HCID 4539NorfloxacinHCID 8471Triethylamine

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a5e0daca0ec14fb9b7e774b7f7eeeb24
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04448962

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