Water → HCID 19371481, compound

HRID 129414Notes

Reaction equation

HRID 129414 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:26])=[C:16]([F:25])[C:17]=2[C:19]#[C:20][Si](C)(C)C)[C:12](=[O:27])[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:10]1.[F-].[K+].O.CN(C)C=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:26])=[C:16]([F:25])[C:17]=2[C:19]#[CH:20])[C:12](=[O:27])[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 19371485HCID 19371485, compound

Product 1

HCID 19371481HCID 19371481, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 4.6 g of ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-8-(trimethylsilylethinyl)-4-oxo-3-quinolinecarboxylate in 20 ml of chloroform is added dropwise at room temperature to a solution of 2 g of potassium fluoride in a solvent mixture of 3 ml of water, 25 ml of chloroform and 50 ml of dimethylformamide. The mixture is stirred for 1 hour at approx. 20° C., the reaction mixture is then treated with more chloroform and extracted several times by shaking with water, and the organic phase is dried and concentrated. The residue obtained is recrystallised from methanol. 3.4 g of ethyl 1-(2,4-difluorophenyl)-8-ethinyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate are obtained (87% of theory).

Workup

  1. extractionextracted several times
  2. stirringby shaking with water
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis recrystallised from methanol

Sources & evidence

ORD record
ord-0007fc3cbaf84ef1b90e255a35c612dc
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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