Ethanol → HCID 54401376, compound

HRID 373325

Reaction equation

HRID 373325 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:19])[C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[N:8]([CH2:20][CH2:21][F:22])[CH:7]=[C:6]([C:23]([OH:25])=[O:24])[C:5]2=O.S(Cl)(Cl)=O.[CH2:31](O)[CH3:32]>>[CH2:31]([O:25][C:23]([C:6]1[CH2:5][C:4]2[C:9](=[C:10]([F:19])[C:11]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[C:2]([F:1])[CH:3]=2)[N:8]([CH2:20][CH2:21][F:22])[CH:7]=1)=[O:24])[CH3:32]

Participants

4

Reactant 3

HCID 702EthanolHCID 3357FleroxacinHCID 24386Thionyl Chloride

Product 1

HCID 54401376HCID 54401376, compoundYield 81%

Procedure

To a stirred suspension of 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (Fleroxacin; Belgian Patent No. 887,574) (35 g, 0.095 mol) in anhydrous ethanol (2.0 L) was added dropwise thionyl chloride (184 mL, 2.52 mol) over a 2-hour period. The solution was then heated at reflux and monitored by thin layer chromatography, until all starting material had been consumed (at this point a clear solution was obtained). The mixture was evaporated to dryness (36.3 g) and recrystallized from ethanol to give a white crystalline solid (30.4 g, 81% yield).

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux
  3. customhad been consumed (at this point a clear solution
  4. customwas obtained)
  5. customThe mixture was evaporated to dryness (36.3 g)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-512ecb3615dc4e8a9e407da07d2db2ca
Source dataset
uspto-grants-1992_11
Patent number
US05162523

Linked notes

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