Hydrogen Peroxide → 2-Chloro-4-methylpyridine 1-oxide
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.OO.C([O-])([O-])=[O:12].[Na+].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N+:3]=1[O-:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
2-chloro-4-methylpyridine (10 g, 80 mmol) was dissolved in acetic acid (100 ml). Hydrogen peroxide (31%, 86.8 g, 80.7 ml, 790 mmol)) was added in 4 portions and the solution stirred under nitrogen at 65° C. for 18 hours. The mixture was poured into ice water (300 ml), and solid Na2CO3 added until the solution was alkaline. The mixture was extracted with DCM (3×300 ml), the organic fractions combined, washed with sodium thiosulfate (1M, 100 ml), brine, dried over Na2SO4, and the volatiles removed in vacuum to give the titled compound.
Workup
- additionadded until the solution
- extractionThe mixture was extracted with DCM (3×300 ml)
- washwashed with sodium thiosulfate (1M, 100 ml), brine
- dry with materialdried over Na2SO4
- customthe volatiles removed in vacuum
Sources & evidence
- ORD record
- ord-6a615a75ed284508a0b89c6529a24c42
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552022B2
Reaction notes
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