Water → Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-8-fluoro-1-(2-hydroxyethyl)-4-oxo-3-quinolinecarboxylate

HRID 491524Notes

Reaction equation

HRID 491524 reaction equation
[Cl:1][C:2]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[N:11]([CH2:16][CH2:17][O:18][Si](C(C)(C)C)(C)C)[CH:10]=[C:9]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:8]2=[O:31].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Cl:1][C:2]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[N:11]([CH2:16][CH2:17][OH:18])[CH:10]=[C:9]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:8]2=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 23083923Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-8-fluoro-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-3-quinolinecarboxylate

Product 1

HCID 23083944Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-8-fluoro-1-(2-hydroxyethyl)-4-oxo-3-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-8-fluoro-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-3-quinolinecarboxylate (350 mg, 0.63 mmol) obtained in Step 5 was dissolved in THF (25 ml), tetrabutylammonium fluoride (1M THF solution; 1.9 ml, 1.9 mmol) was added, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, the precipitated solid was collected by filtration, which was washed with water and vacuum dried to give the object product (279 mg, yield quantitative) as a pale-yellow solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration, which
  2. washwas washed with water and vacuum
  3. customdried
  4. customto give
  5. customthe object product (279 mg, yield quantitative) as a pale-yellow solid

Sources & evidence

ORD record
ord-5412ad45f48943879f13cb15774800b9
Source dataset
uspto-grants-2009_05
Patent number
US07531554B2

Reaction notes

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