Sodium Carbonate → 3-Methylquinolin-8-ol
Reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([CH3:13])=[CH:8]2.C(=O)([O-])[O-].[Na+].[Na+]>Br>[CH3:13][C:9]1[CH:10]=[N:11][C:12]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[CH:4][C:3]=2[OH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 122 °C
Procedure
47% HBr (10 ml) was added to 8-methoxy-3-methylquinoline (Intermediate 29) (500 mg, 2.80 mmol) and heated at 122° C. for 18 h. The reaction was cooled to room temperature, the pH adjusted with sodium carbonate solution to pH=7 and extracted with DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (150 mg, 83%).
Workup
- temperatureThe reaction was cooled to room temperature
- extractionextracted with DCM
- dry with materialThe organic phase was dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c3d07f806a224b27afb62b8d2a4d5e6f
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102688B2
Reaction notes
Loading…