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

HRID 129409Notes

Reaction equation

HRID 129409 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:21])=[C:11]([F:20])[C:12]=3[C:14]#[C:15][Si](C)(C)C)[C:7](=[O:22])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[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](=[CH:9][C:10]([F:21])=[C:11]([F:20])[C:12]=3[C:14]#[CH:15])[C:7](=[O:22])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 522689Potassium FluorideHCID 19371458Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(trimethylsilylethinyl)-4-oxo-3-quinolinecarboxylate

Product 1

HCID 19371453Ethyl 1-cyclopropyl-8-ethinyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.8 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-(trimethylsilylethinyl)-4-oxo-3-quinolinecarboxylate and 9.7 g of potassium fluoride are stirred for 3 hours at room temperature in a mixture of 300 ml of dimethylformamide, 200 ml of chloroform and 15 ml of water. The mixture is then filtered, the filtrate is treated with 120 ml of water, and the mixture is acidified with dilute aqueous hydrochloric acid. After extraction by shaking with chloroform, the organic phase is dried over sodium sulphate and concentrated. The residue obtained is recrystallised from methanol. In this way, 9 g of ethyl 1-cyclopropyl-8-ethinyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (59% of theory) are obtained.

Workup

  1. filtrationThe mixture is then filtered
  2. additionthe filtrate is treated with 120 ml of water
  3. extractionAfter extraction
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customis recrystallised from methanol

Sources & evidence

ORD record
ord-5fa9d220f8604b57a9109b25bddd0fca
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

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