Potassium Carbonate → 8-Chloro-7-(2-methoxyethoxy)-2-methylquinoline

HRID 339000Notes

Reaction equation

HRID 339000 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][O:23][CH3:24]>CC(C)=O>[Cl:1][C:2]1[C:3]([O:13][CH2:21][CH2:22][O:23][CH3:24])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1358589748-Chloro-2-methylquinolin-7-ol

Product 1

HCID 709830998-Chloro-7-(2-methoxyethoxy)-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8-chloro-2-methylquinolin-7-ol (80 mg, 0.41 mmol), potassium carbonate (171 mg, 1.2 mmol) and 1-bromo-2-methoxyethane (115 mg, 0.83 mmol) in acetone (10 mL) were stirred at 70° C. in a sealed tube for 20 hours. After dilution with water (50 mL) the reaction was extracted with DCM. The DCM phases were concentrated under reduced pressure and the residue purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 8-chloro-7-(2-methoxyethoxy)-2-methylquinoline as a solid.

Workup

  1. extractionAfter dilution with water (50 mL) the reaction was extracted with DCM
  2. concentrationThe DCM phases were concentrated under reduced pressure
  3. customthe residue purified by reverse phase chromatography (SP4, 25M
  4. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-cb6694d9264d478d9c5d886681ebee4d
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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