Water → 1-Butyl-2-oxo-quinoline-4-carboxylic acid

HRID 6358Notes

Reaction equation

HRID 6358 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17]CCCC)=[O:16])=[CH:7][C:6]1=[O:22])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O>O1CCOCC1>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]1=[O:22])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 104476011-(n-Butyl)-4-(n-butyloxycarbonyl)-2-oxo-1,2-dihydro-quinoline

Product 1

HCID 2856101-Butyl-2-oxo-quinoline-4-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.04 g (6.77 mmols) of Compound b, 0.54 g of sodium hydroxide, 40 ml of water and 40 mt of dioxane was stirred at room temperature for 30 minutes. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=5/1) to give 1.44 g (yield: 87%) of Compound a.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-0b7ac1002a9c48df9ec7bd4af81498e1
Source dataset
uspto-grants-1993_09
Patent number
US05248684

Reaction notes

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