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

HRID 1517999Notes

Reaction equation

HRID 1517999 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) and tetrabutylammonium fluoride (1M THF solution; 1.9 ml, 1.9 mmol) was added. The mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution and the precipitate was collected by filtration, washed with water and vacuum-dried to give an object product (279 mg, yield quant) as a pale-yellow solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. customvacuum-dried
  4. customto give
  5. customan object product (279 mg, yield quant) as a pale-yellow solid

Sources & evidence

ORD record
ord-9e34470224214110a8fe92085d77c498
Source dataset
uspto-grants-2012_07
Patent number
US08232401B2

Reaction notes

Loading…