Ethyl Acetate → HCID 18426837, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=C(C)[CH:6]=[CH:5]2.[Se](=O)=O.O.[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+].[C:30]([O:33][CH2:34]C)(=[O:32])[CH3:31]>O1CCOCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:31]([CH:30]([O:32][CH3:17])[O:33][CH3:34])[CH:6]=[CH:5]2Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 6-bromoquinaldine (111 mg, 0.500 mmol) in 1,4-dioxane (8 mL) was added selenium dioxide (111 mg, 1.00 mmol), and the mixture was heated at 100° C. for 1 h. The reaction mixture was diluted with ethyl acetate, filtered through Celite pad, and concentrated under reduced pressure. To the residue were added methanol (15 mL) and p-toluenesulfonic acid monohydrate (99 mg, 0.52 mmol), and the mixture was heated to reflux for 1.5 h. Diluted aqueous sodium hydroxide was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 6-bromo-2-(dimethoxymethyl)quinoline (127 mg, 90%).
Workup
- filtrationfiltered through Celite pad
- concentrationconcentrated under reduced pressure
- temperaturethe mixture was heated
- temperatureto reflux for 1.5 h
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried on anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-88c531df13634970bc84482bff074d2c
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06452014B1
Reaction notes
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