Sodium Hydroxide → Laquinimod Sodium

HRID 889612Notes

Reaction equation

HRID 889612 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:25])=[C:5]([C:14]([N:16]([CH2:23][CH3:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15])[C:6](=[O:13])[N:7]2[CH3:12].[OH-].[Na+:27]>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([O-:25])=[C:5]([C:14](=[O:15])[N:16]([CH2:23][CH3:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:6](=[O:13])[N:7]2[CH3:12].[Na+:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54677946Laquinimod

Product 1

HCID 23697158Laquinimod SodiumYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The pH value of a solution of 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide (170 mg, 0.48 mmol, 1.00 equiv) in ethanol (5 ml) was adjusted to 9-10 with a solution of 5M sodium hydroxide. The mixture then was stirred for about 30 min at ambient temperature. The resulting solids were collected by filtration and washed with ethanol to give the title compound as a white solid (70 mg, yield: 39%). 1H NMR (300 MHz, DMSO) δ: 6.84˜7.31 (m, 8H), 3.68 (q, 2H), 3.34 (s, 3H), 1.02 (t, 3H). LC-MS: m/z=357 (M-Na+2H)+

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-5478dba4e30f4eea9d1408794aa938f6
Source dataset
uspto-grants-2012_08
Patent number
US08252933B2

Reaction notes

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