Hydrogen Peroxide → 3-Isopropyl-2-methyl-1-oxidopyridin-1-ium
Reaction equation
[OH:1]O.[CH:3]([C:6]1[C:7]([CH3:12])=[N:8][CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4]>CC(O)=O>[CH:3]([C:6]1[C:7]([CH3:12])=[N+:8]([O-:1])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A 50% solution of hydrogen peroxide (24.89 mL) was slowly added to a solution of 3-isopropyl-2-methyl-pyridine (24.5 g, 183 mmol) (Ishiguro, et al., Yakugaku Zasshi (1958) 78:220) in HOAc (280 mL). The mixture was warmed to 70° C. and stirred for 18 h, then cooled to room temperature and concentrated in vacuo to remove the majority of HOAc. The mixture was basified with a saturated solution of NaHCO3 to pH 12 and extracted with CH2Cl2 (3×150 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford 3-isopropyl-2-methyl-pyridine 1-oxide (26.05 g, 94%) as a yellow oil. 1H NMR (CDCl3) δ 1.24 (d, 6H, J=7.0 Hz), 2.56 (s, 3H), 3.13 (sep, 1H, J=7.0 Hz), 7.06-7.17 (m, 2H), 8.17 (d, 1H, J=6.6 Hz).
Workup
- temperaturecooled to room temperature
- concentrationconcentrated in vacuo
- customto remove the majority of HOAc
- extractionextracted with CH2Cl2 (3×150 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5fcd73f86fce4816afc9ce92a1d244c5
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07501518B2
Reaction notes
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