Sodium Hydroxide → Laquinimod Sodium

HRID 1804755Notes

Reaction equation

HRID 1804755 reaction equation
[CH2:1]([N:3]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:4]([C:6]1[C:7](=[O:19])[N:8]([CH3:18])[C:9]2[C:14]([C:15]=1[OH:16])=[C:13]([Cl:17])[CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].[OH-].[Na+:27]>C(O)C>[CH3:2][CH2:1][N:3]([C:4]([C:6]1[C:7](=[O:19])[N:8]([CH3:18])[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([Cl:17])[C:14]=2[C:15]=1[O-:16])=[O:5])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1.[Na+:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54677946Laquinimod

Product 1

HCID 23697158Laquinimod Sodium

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
27.5 °C

Procedure

N-Ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide (18 gm) and ethanol (180 ml) were stirred at 25-30° C. for 15 minutes followed by the addition of 40% sodium hydroxide solution (5.6 ml) at 25-30° C. in 10 minutes. The resulted clear solution was stirred at 25-30° C. for 20 hours. The precipitated white colored solid was filtered, washed with ethanol (20 ml) and then dried at 55-60° C. to a constant weight to yield 13 gm of laquinimod sodium in crystalline Form A2.

Workup

  1. filtrationThe precipitated white colored solid was filtered
  2. washwashed with ethanol (20 ml)
  3. customdried at 55-60° C. to a constant weight

Sources & evidence

ORD record
ord-ab244f97a0f9408bbc58d648e024c666
Source dataset
uspto-grants-2013_01
Patent number
US08354428B2

Reaction notes

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