Hydrochloric Acid → Laquinimod

HRID 538445Notes

Reaction equation

HRID 538445 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]([CH3:27])[C:13](=[O:26])[CH2:14][C:15]([N:17]([CH2:24][CH3:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[C:3]=1[C:4]([O:6]C)=O.[O-]CC.[Na+].O.Cl>C(O)C>[CH3:25][CH2:24][N:17]([C:15]([C:14]1[C:13](=[O:26])[N:12]([CH3:27])[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]([Cl:1])[C:3]=2[C:4]=1[OH:6])=[O:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723922Sodium ethoxideHCID 67609478HCID 67609478, compound

Product 1

HCID 54677946LaquinimodYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (9) (5 mmol) dissolved in dry ethanol (25 ml) at 5° C. was added sodium ethoxide (0.37 g, 5.2 mmol). The mixture was stirred at this temperature for 1 h, and then at room temperature under TLC control. After completion of the reaction (˜2-3 h) [if the reaction was not completed by this time, the mixture was further refluxed for an additional 1-2 h], water (100 ml) was slowly added followed by a drop-wise addition of 1.0 N hydrochloric acid (6 ml) with stirring. After 30 minutes at 5° C., the crystals were collected by filtration, washed with water, and dried at 40° C. under vacuum to give (1) in 79% yield with an assay of 98.6%.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction (˜2-3 h) [if the reaction
  3. additionwas slowly added
  4. stirringwith stirring
  5. waitAfter 30 minutes at 5° C.
  6. filtrationthe crystals were collected by filtration
  7. washwashed with water
  8. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-db720cdae3fc4d629deb14b9e3b2334e
Source dataset
uspto-grants-2014_10
Patent number
US08865742B2

Reaction notes

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