Methanol → 2-(1-Hydroxy-2-nonynyl)-3-methyl-6-fluoro-4-quinolone

HRID 1613939Notes

Reaction equation

HRID 1613939 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)[C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CO>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)[C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 150070622-(1-Hydroxy-2-nonynyl)-3-methyl-4-acetoxy-6-fluoroquinoline

Product 1

HCID 678323882-(1-Hydroxy-2-nonynyl)-3-methyl-6-fluoro-4-quinoloneYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 135 mg (0.978 mmols) of potassium carbonate in 1 ml of water was added to a solution of 349 mg (0.978 mmols) of 2-(1-hydroxy-2-nonynyl)-3-methyl-4-acetoxy-6-fluoroquinoline, 20 ml of methanol and 2 ml of water and stirred at room temperature for 10 minutes. After neutralization with 1N hydrochloric acid, the solvent was distilled off under reduced pressure, followed by addition of 20 ml of chloroform to the resultant residue, washing with water and drying with sodium sulfate. The solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (Wako gel C-200) (solvent: n-hexane : ethyl acetate=1:1) to obtain 183 mg (yield 59 %) of 2-(1-hydroxy-2-nonynyl)-3-methyl-6-fluoro-4-quinolone.

Workup

  1. distillationAfter neutralization with 1N hydrochloric acid, the solvent was distilled off under reduced pressure
  2. additionfollowed by addition of 20 ml of chloroform to the resultant residue
  3. washwashing with water
  4. dry with materialdrying with sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customfollowed by purification by silica gel column chromatography (Wako gel C-200) (solvent: n-hexane : ethyl acetate=1:1)

Sources & evidence

ORD record
ord-22169784fe294915aa395e73ae00e15a
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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