1,3-Dimethyl-2-imidazolidinone → 4-Methoxy-2-methylquinolin-8-ol
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.CN1CCN(C)[C:16]1=[O:21].C[O-].[Na+]>CO>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[O:21][CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 4-chloro-8-hydroxy-2-methylquinoline (9 g), 1,3-dimethyl-2-imidazolidinone (100 ml) and 28% solution of sodium methoxide in methanol (135 ml) was stirred at 150° C. for 4 hours. The reaction mixture was cooled to ambient temperature followed by partition into ethyl acetate and water. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The crystalline residue was washed with n-hexane to give 8-hydroxy-4-methoxy-2-methylquinoline (5.57 g).
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- customby partition into ethyl acetate and water
- washThe organic layer was washed with water and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- washThe crystalline residue was washed with n-hexane
Sources & evidence
- ORD record
- ord-c67fb0c56a1845a78f191339042bb2c6
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06169095A
Reaction notes
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