Hydrogen Peroxide → 4-Methoxy-2,3,5-trimethylpyridine 1-oxide
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH3:10])[C:4]=1[CH3:11].[OH:12]O>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N+:6]([O-:12])=[C:5]([CH3:10])[C:4]=1[CH3:11]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
100 g 4-methoxy-2,3,5-trimethylpyridine was dissolved in 300 ml glacial acetic acid and 100 ml 50% hydrogenperoxide and stirred at 30° C. for 1 h. The temperature was gradually heated to70° C. and was maintained for 5 hrs and the temperature increased to 90° C. and a small amount of Pd/C added to destroy excess hydrogenperoxide. After testing that the peroxide was destroyed the solvents were evaporated at reduced pressure. Toluene was added and stripped off to make the product free from water. After the product was dry most of the toluene was evaporated in vacuum. The 4-methoxy-2,3,5-trimethylpyridine N-oxide was diluted with acetic acid and used directly in the next step. The yield of N-oxide was 95%.
Workup
- temperatureand was maintained for 5 hrs
- customto destroy excess hydrogenperoxide
- customwas destroyed the solvents
- customwere evaporated at reduced pressure
- additionToluene was added
- dry with materialAfter the product was dry most of the toluene
- customwas evaporated in vacuum
- additionThe 4-methoxy-2,3,5-trimethylpyridine N-oxide was diluted with acetic acid
Sources & evidence
- ORD record
- ord-4007545b6ec0477990b7676aa0035216
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04785113
Reaction notes
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