Sodium Hydroxide → Laquinimod Sodium

HRID 1804756Notes

Reaction equation

HRID 1804756 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)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 SodiumYield 67.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-Ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide (15 gm) was suspended in isopropyl alcohol (100 ml) at 25-30° C. under stirring followed by the addition of freshly prepared sodium hydroxide solution (1.4 gm of sodium hydroxide in 3.5 ml of water) at 20-25° C. and then stirred for 15-30 minutes at 25-30° C. The resulting solution was filtered through a hyflow supercell bed and the bed was washed with isopropyl alcohol (50 ml) at 25-30° C. The resulting filtrate was stirred for 20 hours at 25-30° C. The resulting white colored solid was filtered, washed with chilled isopropyl alcohol (20 ml) and then dried in air oven at 60-65° C. to yield 9 gm of laquinimod sodium in crystalline Form A2 (HPLC Purity: 99.8%).

Workup

  1. stirringstirred for 15-30 minutes at 25-30° C
  2. filtrationThe resulting solution was filtered through a hyflow supercell bed
  3. washthe bed was washed with isopropyl alcohol (50 ml) at 25-30° C
  4. stirringThe resulting filtrate was stirred for 20 hours at 25-30° C
  5. filtrationThe resulting white colored solid was filtered
  6. washwashed with chilled isopropyl alcohol (20 ml)
  7. customdried in air oven at 60-65° C.

Sources & evidence

ORD record
ord-f6a2a2362a9344eba17de9a6ac8f8470
Source dataset
uspto-grants-2013_01
Patent number
US08354428B2

Reaction notes

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