Hydrochloric Acid → 2-(trans-1-Hydroxy-2-nonenyl)-3-methyl-6-fluoro-4-quinolone

HRID 1613941Notes

Reaction equation

HRID 1613941 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][CH:8]([C:17]1[C:26]([CH3:27])=[C:25]([O:28]C(=O)C)[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:32])[CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CO.Cl>O>[OH:7][CH:8]([C:17]1[CH:26]([CH3:27])[C:25](=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:32])[CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 150070632-(trans-1-Hydroxy-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline

Product 1

HCID 867466312-(trans-1-Hydroxy-2-nonenyl)-3-methyl-6-fluoro-4-quinoloneYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 715 mg (5.18 mmols) of potassium carbonate in 3 ml of water was added to a solution of 1.86 g (5.18 mmols) of 2-(trans-1-hydroxy-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline, 50 ml of methanol and 2 ml of water and stirred at room temperature for 10 minutes. After neutralization by addition of 1N hydrochloric acid, the solvent was distilled off under reduced pressure and 30 ml of chloroform was added to the resultant residue, followed by washing with water and drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (solvent: chloroform : methanol=40:1) to obtain 1.19 g (yield 72 %) of 2-(trans-1-hydroxy-2-nonenyl)-3-methyl-6-fluoro-4-quinolone.

Workup

  1. distillationthe solvent was distilled off under reduced pressure and 30 ml of chloroform
  2. additionwas added to the resultant residue
  3. washby washing with water
  4. dry with materialdrying with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (solvent: chloroform : methanol=40:1)

Sources & evidence

ORD record
ord-aece128e6fbb414aa508fe8a0386b301
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

Loading…