Acetone → 7-(2-Methoxyethoxy)-2-methylquinoline
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:14][CH2:15][O:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[CH3:17][O:16][CH2:15][CH2:14][O:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 2-methylquinolin-7-ol (0.20 g, 1.3 mmol), 1-bromo-2-methoxyethane (0.24 mL, 2.5 mmol) and potassium carbonate (0.52 g, 3.8 mmol) in acetone (5.0 mL, 1.3 mmol) was heated at 70° C. for 12 hours. The cooled reaction mixture was diluted with water (10 mL) extracted with dichloromethane (3×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by normal phase chromatography on silica gel (10-50% ethyl acetate/hexanes) to provide title compound (0.16 g, 60%).
Workup
- customThe cooled reaction mixture
- extractionextracted with dichloromethane (3×20 mL)
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by normal phase chromatography on silica gel (10-50% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-09796c40ed234eea8b80c679183e85c9
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889704B2
Reaction notes
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