Ethanol → HCID 12733925, compound

HRID 544215Notes

Reaction equation

HRID 544215 reaction equation
S(Cl)(Cl)=O.[OH:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([F:27])=[C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]3)[CH:16]=2)[C:11](=[O:28])[C:10]([C:29]([OH:31])=[O:30])=[CH:9]1.[CH2:32](O)[CH3:33]>>[CH2:32]([O:30][C:29]([C:10]1[C:11](=[O:28])[C:12]2[C:17](=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]3)=[C:14]([F:27])[CH:13]=2)[N:8]([CH2:7][CH2:6][OH:5])[CH:9]=1)=[O:31])[CH3:33]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 12733936HCID 12733936, compound

Product 1

HCID 12733925HCID 12733925, compound

Procedure

Thionyl chloride (2.4 g) was added dropwise to a solution of 1-(2-hydroxyethyl)-6-fluoro-7-(4-acetyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.38 g) in ethanol (20 ml) under cooling with an ice-water bath, and the reaction mixture was refluxed for 5.5 hrs. The reaction mixture was evaporated to dryness, the residue was neutralized with aqueous potassium carbonate solution, and the solution was extracted with chloroform. After removing the chloroform, the residue was recrystallized from a mixture of methylene chloride and ethyl acetate to give 0.36 g of 1-(2-hydroxyethyl)-6-fluoro-7-(4-acetyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester.

Workup

  1. temperatureunder cooling with an ice-water bath
  2. temperaturethe reaction mixture was refluxed for 5.5 hrs
  3. customThe reaction mixture was evaporated to dryness
  4. extractionthe solution was extracted with chloroform
  5. customAfter removing the chloroform
  6. customthe residue was recrystallized from a mixture of methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-ad8d719118094a589022ce279d0e7cf0
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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