2,3-Lutidine → Pyridine, 2,3-dimethyl-, 1-oxide

HRID 659988Notes

Reaction equation

HRID 659988 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8].ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)(Cl)Cl>[N+:1]1([O-:17])[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8]

Participants

4

Reactant 2

HCID 114202,3-LutidineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 3840573Pyridine, 2,3-dimethyl-, 1-oxideYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2,3-lutidine (5.00 g, 46.7 mmol) in chloroform (100 mL) at 0° C. was added m-chloroperbenzoic acid (12.0 g of a 77% max reagent) portionwise over 5 min. The reaction mixture was stirred for an additional 30 min at 0° C. and then allowed to warm to room temperature. After 16 h, the reaction mixture was concentrated to dryness, water (20 mL) was added and the pH of the mixture was adjusted to 8 (saturated NaHCO3). The mixture was concentrated and the residue was extracted with dichloromethane/methanol (4:1). The extracts were concentrated to a white solid. Subsequent column purification (SiO2; dichloromethane/methanol, 9:1) gave 2,3-lutidine-N-oxide as a white solid (4.80 g, 83%).

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 16 h
  3. concentrationthe reaction mixture was concentrated to dryness, water (20 mL)
  4. additionwas added
  5. concentrationThe mixture was concentrated
  6. extractionthe residue was extracted with dichloromethane/methanol (4:1)
  7. concentrationThe extracts were concentrated to a white solid
  8. customSubsequent column purification (SiO2; dichloromethane/methanol, 9:1)

Sources & evidence

ORD record
ord-fc8938b57b934513855dceb6225589a0
Source dataset
uspto-grants-2011_12
Patent number
US08084459B2

Reaction notes

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