Water → Ethyl 1-cyclopropyl-5-ethinyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 2258123Notes

Reaction equation

HRID 2258123 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([C:17]#[C:18][Si](C)(C)C)[C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:23])[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1.[F-].[K+].C(Cl)(Cl)Cl.O>CN(C)C=O>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([C:17]#[CH:18])[C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:23])[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6212Chloroform2×HCID 522689Potassium FluorideHCID 22924385Ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-trimethylsilylethinyl-4-oxo-3-quinolinecarboxylate

Product 1

HCID 22924399Ethyl 1-cyclopropyl-5-ethinyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1 g of the product of Example E and 0.45 g of potassium fluoride are stirred for 1 hour at room temperature in a mixture of 20 ml of dimethylformamide, 10 ml of chloroform and 1 ml of water. After chloroform has been added, the organic phase is separated off, extracted by shaking with water, dried over sodium sulphate and concentrated. The residue is boiled briefly in 20 ml of methanol. When the mixture has cooled to 0° C., the solid obtained is filtered off with suction and dried. 0.63 g of the title compound is obtained (77% of theory).

Workup

  1. customthe organic phase is separated off
  2. extractionextracted
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customthe solid obtained
  6. filtrationis filtered off with suction
  7. customdried

Sources & evidence

ORD record
ord-154cf26683fe41bb8039c34990ddd31d
Source dataset
uspto-grants-1997_08
Patent number
US05659038

Reaction notes

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