N-Ethylaniline → Laquinimod

HRID 889611Notes

Reaction equation

HRID 889611 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13]([OH:28])=[C:14]([C:23]([O:25]CC)=O)[C:15](=[O:22])[N:16]2[CH3:21]>CCCCCCC>[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13]([OH:28])=[C:14]([C:23]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:25])[C:15](=[O:22])[N:16]2[CH3:21]

Participants

4

Reactant 2

HCID 7670N-EthylanilineHCID 54717770Ethyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 54677946LaquinimodYield 60%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
100 °C

Procedure

N-ethylbenzenamine (430 mg, 3.55 mmol, 2.00 equiv) was added dropwise to ethyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (500 mg, 1.78 mmol, 1.00 equiv) dissolved in heptane (10 ml). The resulting mixture was heated about 100° C. and the volatiles were removed by distillation over a period of about 7 hours. After cooling to ambient temperature, the resulting crystals were collected by filtration, washed with heptane, and purified by silica gel chromatography (ethyl acetate/petroleum ether 1:3) to afford the title product as a white solid (0.38 g, yield: 60%).

Workup

  1. customthe volatiles were removed by distillation over a period of about 7 hours
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with heptane
  5. custompurified by silica gel chromatography (ethyl acetate/petroleum ether 1:3)

Sources & evidence

ORD record
ord-45b9f0e8df2f493580fb5c4b1c620609
Source dataset
uspto-grants-2012_08
Patent number
US08252933B2

Reaction notes

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