Ethanol → 1-(4-Fluorophenyl)-1,4-di-hydro4-oxo-7-(4-pyridinyl)-3-quinolinecarboxylic acid

HRID 1032716Notes

Reaction equation

HRID 1032716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[CH:16]=3)[C:11](=[O:24])[C:10]([C:25]([O:27]CC)=[O:26])=[CH:9]2)=[CH:4][CH:3]=1.[OH-].[K+].C(O)C>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[CH:16]=3)[C:11](=[O:24])[C:10]([C:25]([OH:27])=[O:26])=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 10023142Ethyl 1-(4-fluorophenyl)1,4-dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxylate

Product 1

HCID 103385501-(4-Fluorophenyl)-1,4-di-hydro4-oxo-7-(4-pyridinyl)-3-quinolinecarboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.8 g of ethyl 1-(4-fluorophenyl)1,4 -dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxylate, 20 ml of 10% potassium hydroxide solution and 10 ml ethanol was heated on a steam bath for 3 hrs. The reaction mixture was cooled and acidified with acetic acid. The solid product was collected and washed with acetone to give 2.6 g 1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxylic acid. A sample of the compound was converted to its monomethanesulfonate salt, m.p. 280-281° C. when recrystallized from acetonitrile.

Workup

  1. temperaturewas heated on a steam bath for 3 hrs
  2. temperatureThe reaction mixture was cooled
  3. customThe solid product was collected
  4. washwashed with acetone

Sources & evidence

ORD record
ord-5a004ab8773144f9ac7ad6412473c887
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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