Pyridine → Ethyl norfloxacin

HRID 2418467Notes

Reaction equation

HRID 2418467 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][C:17](Cl)=[C:18]([F:23])[CH:19]=2)[N:14]([CH2:25][CH3:26])[CH:13]=1)=[O:11])[CH3:8].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:7]([O:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][C:17]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)=[C:18]([F:23])[CH:19]=2)[N:14]([CH2:25][CH3:26])[CH:13]=1)=[O:11])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4837PiperazineHCID 12733855Ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Product 1

HCID 12733941Ethyl norfloxacinYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Anhydrous piperazine (10.3 g) and 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester were added to a mixture of pyridine (9 ml) and toluene (18 ml), and the mixture was refluxed with stirring for 5 hrs. The same procedure as described in Example 1 was followed to give 8.4 g (81% yield) of 1-ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester. mp: 178.5°-180° C.

Workup

  1. temperaturethe mixture was refluxed

Sources & evidence

ORD record
ord-3e97d868a0124c268975c6dfb5d2d820
Source dataset
uspto-grants-1984_09
Patent number
US04472579

Reaction notes

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