Water → Dibucaine IMpurity D

HRID 1109166Notes

Reaction equation

HRID 1109166 reaction equation
[CH2:1]([O:5][C:6]1[CH:15]=[C:14]([C:16]([O:18]CCCC)=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O>O1CCOCC1>[CH2:1]([O:5][C:6]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11779624Butyl 2-butoxy-4-quinolinecarboxylate

Product 1

HCID 10014750Dibucaine IMpurity DYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.67 g (8.86 mmols) of Compound b, 1.77 g of sodium hydroxide, 60 ml of water and 60 ml of dioxane was stirred at room temperature for an hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluting solvent: chloroform/methanol=5/1) to give 1.91 g (yield 90%) of Compound a.

Workup

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

Sources & evidence

ORD record
ord-4801f70a26024351b36c888027d16128
Source dataset
uspto-grants-1994_06
Patent number
US05319085

Reaction notes

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