Sodium Hydroxide → Laquinimod sodium

HRID 511944Notes

Reaction equation

HRID 511944 reaction equation
[CH3:1][CH2:2][N:3]([C:10]([C:12]1[C:22](=[O:23])[N:21]([CH3:24])[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=2[C:13]=1[OH:25])=[O:11])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[OH-].[Na+:27].[Na]>C(O)C>[CH3:1][CH2:2][N:3]([C:10]([C:12]1[C:22](=[O:23])[N:21]([CH3:24])[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=2[C:13]=1[O-:25])=[O:11])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[Na+:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 54677946Laquinimod

Product 1

HCID 23697158Laquinimod sodiumYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Deuterated laquinimod prepared in Step 2 was suspended in ethanol and treated with 20% aqueous NaOH solution. The precipitated sodium salt was stirred for 3 hours, filtered and washed with ethanol. Drying in vacuum provided deuterated laquinimod sodium salt (92-94% yield). Identity and purity were proven by NMR, MS and HPLC.

Workup

  1. filtrationfiltered
  2. washwashed with ethanol
  3. customDrying in vacuum

Sources & evidence

ORD record
ord-6ce2ebebd69d4bffb31b79b88f2ebf5d
Source dataset
uspto-grants-2015_08
Patent number
US09102620B2

Reaction notes

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