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

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

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.