N-Ethylaniline → Laquinimod

HRID 227555Notes

Reaction equation

HRID 227555 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 8900Heptane2×HCID 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. 2.88 ml), and heptane (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-6059b5139f494f0682de4d2d06b098b3
Source dataset
uspto-grants-2009_07
Patent number
US07560557B2

Reaction notes

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