m-Chloroperbenzoic acid → HCID 57811609, compound

HRID 469239Notes

Reaction equation

HRID 469239 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]1([NH:18][C:19]2[CH:28]=[C:27]3[C:22]([C:23](=[O:36])[C:24](C=O)=[CH:25][N:26]3[CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:21][C:20]=2[F:37])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])O.[Na+]>ClCCl>[CH:12]1([NH:18][C:19]2[CH:28]=[C:27]3[C:22]([C:23](=[O:36])[C:24]([OH:9])=[CH:25][N:26]3[CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)=[CH:21][C:20]=2[F:37])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 866330517-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde

Product 1

HCID 57811609HCID 57811609, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.1 g of metachloroperbenzoic acid was gradually added to a 100 ml of dichloromethane solution of 8.0 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde at room temperature, followed by stirring for 2 hours. Aqueous saturated sodium hydrogen carbonate and aqueous sodium hydrogenthiosulfate were added to the reaction mixture, followed by stirring for 30 minutes and then extraction with chloroform. After drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure, the residue was purified by silica gel column chromatography to obtain 7.7 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-hydroxyquinolin-4(1H)-one.

Workup

  1. stirringby stirring for 30 minutes
  2. extractionextraction with chloroform
  3. dry with materialAfter drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7eeed1714869412793485857e4f97421
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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