Sodium Hydroxide → Laquinimod Sodium

HRID 1039626Notes

Reaction equation

HRID 1039626 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

Laquinimod (2.7 gm) was taken in ethanol (13 ml) and stirred at 25-30° C. followed by the addition of sodium hydroxide solution (0.33 gm of NaOH in 0.4 ml of water). The resulting solution was stirred for 15 minutes followed by filtration through hyflow bed and washing of the bed with ethanol (7 ml). The resulting clear solution was then stirred for 16 hours at 25-30° C. The separated solid was filtered, washed with chilled ethanol (2 ml) and then dried at 60-65° C. to yield 2.33 gin of laquinimod sodium as a white solid (HPLC Purity: 99.92%).

Workup

  1. stirringThe resulting solution was stirred for 15 minutes
  2. filtrationfollowed by filtration through hyflow bed
  3. washwashing of the bed with ethanol (7 ml)
  4. stirringThe resulting clear solution was then stirred for 16 hours at 25-30° C
  5. filtrationThe separated solid was filtered
  6. washwashed with chilled ethanol (2 ml)
  7. customdried at 60-65° C.

Sources & evidence

ORD record
ord-17eb902369744bf5870a0cb56398b7c8
Source dataset
uspto-grants-2013_10
Patent number
US08552194B2

Reaction notes

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