Dichloromethane → 3-Acetoxy-8-methoxy quinoline
Reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13].C(N(CC)CC)C.ClCCl.[C:24](Cl)(=[O:26])[CH3:25]>O>[C:24]([O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[O:12][CH3:13])(=[O:26])[CH3:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
175 mg of 3-hydroxy-8-methoxy quinoline [compound (V)] prepared in example 6 and 132 mg of triethyl amine were added to 10 ml of dichloromethane. After cooled to 0° C., 0.1 ml of acetyl chloride was slowly added dropwise. The solution was agitated for 1 hour, and water was added to the solution. The solution was extracted with dichloromethane and washed with water. The dichloromethane layer was dried with anhydrous magnesium sulfate. The dichloromethane was removed by vacuum distillation to give 195 mg of 3-acetoxy-8-methoxy quinoline as an oil.
Workup
- extractionThe solution was extracted with dichloromethane
- washwashed with water
- dry with materialThe dichloromethane layer was dried with anhydrous magnesium sulfate
- customThe dichloromethane was removed by vacuum distillation
Sources & evidence
- ORD record
- ord-39fa172cb72648fe9375f59f6e330b81
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05824689
Reaction notes
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