Water → 1-Ethyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 544237Notes

Reaction equation

HRID 544237 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].[N:24]([O-])=[O:25].[Na+].O>C(O)(=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]([N:24]=[O: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]

Participants

5

Reactant 3

HCID 962WaterHCID 4539NorfloxacinHCID 23668193Sodium Nitrite

Product 1

HCID 133204561-Ethyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.2 g (10 millimole) of 1-ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was dissolved in 30 ml of acetic acid, and 1.4 g (20 millimole) of sodium nitrite was added slowly thereto at room temperature under stirring. After stirring for 30 minutes at room temperature, 50 ml of water was added. The precipitated crystals were collected by filtration, washed successively with water, ethanol and dichloromethane and dried. 3.5 g (quantitative) of 1-ethyl-6-fluoro-7-(4-nitroso-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was obtained as grayish colorless powders.

Workup

  1. stirringAfter stirring for 30 minutes at room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed successively with water, ethanol and dichloromethane
  4. customdried

Sources & evidence

ORD record
ord-c00bb0e3055440319cb0f09a1cc42553
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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