Dichloromethane → 4-Allyloxy-6-methoxy-quinoline
Reaction equation
[Na].[CH2:2]([OH:5])[CH:3]=[CH2:4].Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][CH:8]=1.ClCCl>CO>[CH2:2]([O:5][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[CH:9][CH:8]=1)[CH:3]=[CH2:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium (1.22 g, 52.9 mmol, 2.1 eq) is added portionwise at 0° C. to a stirred solution of allyl alcohol (117.1 g, 201.6 mmol, 80.0 eq). After 30 minutes stirring at 0° C., 4-bromo-6-methoxy-quinoline (6.0 g, 25.2 mmol, 1.0 eq) is added to the reaction mixture that is heated under reflux for 5 hours. The reaction mixture is then cooled down to room temperature, and filtered. The filtrate is evaporated under reduced pressure to give a residue that is extracted with ethyl acetate (3×100 mL) and water (100 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 60:1, v/v) to afford 4-allyloxy-6-methoxy-quinoline as a white solid (4.0 g, 74% yield).
Workup
- temperatureis heated
- temperatureunder reflux for 5 hours
- temperatureThe reaction mixture is then cooled down to room temperature
- filtrationfiltered
- customThe filtrate is evaporated under reduced pressure
- customto give a residue that
- extractionis extracted with ethyl acetate (3×100 mL) and water (100 mL)
- dry with materialThe combined organic layers are dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give a crude product that
- customis purified by column chromatography (silica gel, eluent
Sources & evidence
- ORD record
- ord-8ea51da44f354edd86427e0b77c4dbfe
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321788B2
Reaction notes
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