Sodium ethoxide → Laquinimod Sodium

HRID 538444Notes

Reaction equation

HRID 538444 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]([C:14](=[O:27])[CH2:15][C:16]([N:18]([CH2:25][CH3:26])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[CH3:13])[C:3]=1[C:4](OC)=[O:5].[O-]CC.[Na+:31]>C(O)C>[CH3:26][CH2:25][N:18]([C:16]([C:15]1[C:14](=[O:27])[N:12]([CH3:13])[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=2[C:4]=1[O-:5])=[O:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+:31]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 67609478HCID 67609478, compound

Product 1

HCID 23697158Laquinimod SodiumYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

Methyl 2-chloro-6-[[3-(ethyl(phenyl)amino)-3-oxo-propanoyl]-methyl-amino]benzoate (Inter-V) (1.5 g, 3.858 mmol) and anhydrous ethanol (40 ml) were added to a round bottom flask at 20-25° C. under nitrogen atmosphere, and the mixture was stirred under nitrogen till a clear solution was obtained. The solution was cooled to 0-5° C., and a 21 wt % solution of sodium ethoxide was added (1.51 ml, 4.051 mmol) keeping the temperature at 0-5° C. while stirring. The mixture was stirred for an additional 1 h at 0-5° C., and the flask was placed in the refrigerator for 12 hours. The precipitate was filtered to obtain a white powder which was dried at 25° C. under vacuum. Yield: 90%. The purity of the isolated product was 100% (HPLC, area %).

Workup

  1. customwas obtained
  2. customat 0-5° C.
  3. stirringwhile stirring
  4. stirringThe mixture was stirred for an additional 1 h at 0-5° C.
  5. filtrationThe precipitate was filtered
  6. customto obtain a white powder which
  7. customwas dried at 25° C. under vacuum

Sources & evidence

ORD record
ord-bc732a045f8742aaa4c01017a15ef29c
Source dataset
uspto-grants-2014_10
Patent number
US08865742B2

Reaction notes

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