Reaction equation
[Na].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CO.CS(C)=O>[CH2:10]([O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:9])=[N:7][CH:8]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3.3 g of sodium were dissolved in 60 ml of methanol and stirred with 15 g of 5-hydroxy-2-methylpyridine in 230 ml of DMSO for 1 hour at a temperature of 80° to 90° C. The methanol was spun or rotated out after cooling the mixture. 23.5 g of benzylbromide were then added, followed by stirring for 20 hours at room temperature. The reaction mixture was then acidified with 2N HCL and mixed with 1500 ml of water. The mixture was then extracted with diethyl ether and the ether phase was discarded. The pH-value of the aqueous phase was then adjusted to approximately 8 and the solution was extracted with ether. The organic phase was evaporated. 24.1 g of 5-benzyloxy-2-methylpyridine were obtained. The latter was dissolved in 200 ml of glacial acetic acid, mixed with 12 ml of hydrogen peroxide (30%) and refluxed for 2 hours. The mixture was then neutralized with 40% caustic soda solution and 1000 ml of water were added. The solution was extracted with dichloromethane and the organic phase evaporated. 25 g of 5-benzyloxy-2-methylpyridine-N-oxide were obtained.
Workup
- temperatureafter cooling the mixture
- extractionThe mixture was then extracted with diethyl ether
- extractionthe solution was extracted with ether
- customThe organic phase was evaporated
Sources & evidence
- ORD record
- ord-35e2cbeb83b847829fc3d6876b5d72b3
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997835
Linked notes
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