Hydrogen Peroxide → HCID 22929836, compound
Reaction equation
OO.[CH3:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][N:11]=[N+:12]=[N-:13])=[CH:6][CH:5]=1.C1(=O)OC(=[O:18])C=C1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[N:11]([CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[N+:9]([O-:18])[CH:8]=1)=[N+:12]=[N-:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
After adding 30% aqueous hydrogen peroxide (7.5 ml, 6.6 mmol) dropwise to a solution of (6-methyl-3-pyridyl)methyl azide (8.9 g, 6.0 mmol) and maleic anhydride (6.5 g, 6.6 mmol) in methylene chloride (90 ml) over a period of 5 minutes while cooling on ice, the mixture was stirred at room temperature for 16 hours. Maleic anhydride (3.25 g) and 30% aqueous hydrogen peroxide (3.75 ml) were added in a similar manner while cooling on ice, and the mixture was stirred at room temperature for 4 hours. Saturated aqueous sodium hydrogencarbonate (100 ml) was added to the reaction mixture, NaHCO3 was further added to be basic, and extraction was performed with methylene chloride. The extract was washed with a brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off to yield crude 5-(azidomethyl)-2-methyl-1-pyridiniumolate (7.45 g). This was used without further purification for the following reaction.
Workup
- temperaturewhile cooling on ice
- temperaturewhile cooling on ice
- stirringthe mixture was stirred at room temperature for 4 hours
- additionwas further added
- extractionextraction
- washThe extract was washed with a brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-cee71b0b52714061b486cd18f901a220
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07244730B2
Reaction notes
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