Potassium Fluoride → HCID 10472113, compound

HRID 1032725Notes

Reaction equation

HRID 1032725 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]#[C:19][Si](C)(C)C)[CH:16]=3)[C:11](=[O:24])[C:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:9]2)=[CH:4][CH:3]=1.[F-].[K+]>C(O)C>[C:18]([C:15]1[CH:16]=[C:17]2[C:12]([C:11](=[O:24])[C:10]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:9][N:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:13][CH:14]=1)#[CH:19]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 10024380HCID 10024380, compound

Product 1

HCID 10472113HCID 10472113, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 23.3 g ethyl 1,4-dihydro-1-(4-fluorophenyl)-4-oxo-7-(trimethylsilylethynyl)-3-quinolinecarboxylate, 10.5 g potassium fluoride and 700 ml ethanol was heated at reflux for 4 hrs. The reaction mixture was concentrated in vacuo and the residue triturated with chloroform. The chloroform-soluble fraction was isolated and recrystallized from ethyl acetate to give 14.02 g ethyl 1,4-dihydro-7-ethynyl-1-(4-fluorophenyl)-4-oxo-3quinolinecarboxylate, m.p. 227°-229° C. d) 1,4-dihydro-1-(4-fluorophenyl)-7-(3-methyl-5

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hrs
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue triturated with chloroform
  5. customThe chloroform-soluble fraction was isolated
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-69da8f96e74646c4bc80782a42e6bbf2
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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