Sodium Hydroxide → 1-Ethyl-6-fluoro-7-[3-(fluoromethyl)-4-methyl-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165621Notes

Reaction equation

HRID 2165621 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:21])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH:15]([CH2:19][F:20])[CH2:14]3)[CH:11]=2)[C:6](=[O:22])[C:5]([C:23]([OH:25])=[O:24])=[CH:4]1)[CH3:2].[CH:26]([O-])=O.[Na+].[OH-].[Na+]>C(O)(=O)C.C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:21])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:26])[CH:15]([CH2:19][F:20])[CH2:14]3)[CH:11]=2)[C:6](=[O:22])[C:5]([C:23]([OH:25])=[O:24])=[CH:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723810Sodium FormateHCID 14839365HCID 14839365, compound

Product 1

HCID 148393661-Ethyl-6-fluoro-7-[3-(fluoromethyl)-4-methyl-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 712FormaldehydeSolvent

Procedure

A 100 mg portion of 1-ethyl-6-fluoro-7-[3-(fluoromethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 300 mg of sodium formate were dissolved in a mixture of 3 ml of glacial acetic acid and 3 ml of 37% formaldehyde and refluxed overnight. The mixture was cooled, basified with sodium hydroxide, acidified with glacial acetic acid and evaporated. The residue was triturated with hot chloroform and the solid crystallized from methanol, giving 91 mg of the desired product, mp 230°-235° C. (dec.).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was cooled
  3. customevaporated
  4. customThe residue was triturated with hot chloroform
  5. customthe solid crystallized from methanol

Sources & evidence

ORD record
ord-b8cff32e3ef74524b4822880ff60b3b5
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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