N-Ethylaniline → Laquinimod

HRID 1814218Notes

Reaction equation

HRID 1814218 reaction equation
CO[C:3]([C:5]1[C:6](=[O:18])[N:7]([CH3:17])[C:8]2[C:13]([C:14]=1[OH:15])=[C:12]([Cl:16])[CH:11]=[CH:10][CH:9]=2)=[O:4].[CH2:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:20].CCCCCCC>CO>[CH2:19]([N:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:3]([C:5]1[C:6](=[O:18])[N:7]([CH3:17])[C:8]2[C:13]([C:14]=1[OH:15])=[C:12]([Cl:16])[CH:11]=[CH:10][CH:9]=2)=[O:4])[CH3:20]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 8900HeptaneHCID 54680901HCID 54680901, compound

Product 1

HCID 54677946LaquinimodYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester (3.0 g), N-ethylaniline (2 eq 2-2.88 ml), and heptaue (60 ml) were heated and the volatiles, mainly heptane and formed methanol, (32 ml) distilled off during 6 hours and 35 minutes. After cooling to room temperature the crystalline suspension was filtered and the crystals were washed with heptane and dried in vacuum to yield the crude title compound (3.94 g, 98%) as white to off-white crystals.

Workup

  1. distillationdistilled off during 6 hours and 35 minutes
  2. filtrationwas filtered
  3. washthe crystals were washed with heptane
  4. customdried in vacuum

Sources & evidence

ORD record
ord-b86c1311bb1442f3a630e6ff679e0285
Source dataset
uspto-grants-2005_04
Patent number
US06875869B2

Reaction notes

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