Nitric Acid → 2,6-Lutidine, 4-nitro-, 1-oxide

HRID 2071155

Reaction equation

HRID 2071155 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N+:3]=1[O-:9].C(Cl)(Cl)Cl.O.[N+:15]([O-])([OH:17])=[O:16]>OS(O)(=O)=O>[CH3:1][C:2]1[CH:7]=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[C:4]([CH3:8])[N+:3]=1[O-:9]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 6212ChloroformHCID 140832,6-Dimethylpyridine N-oxide

Product 1

HCID 209452,6-Lutidine, 4-nitro-, 1-oxideYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2.23 g (18.1 mmol) of 2,6-dimethylpyridine 1-oxide (Alfa Aesar) in 7 mL of H2SO4 and 2.7 mL of HNO3 was stirred at 130° C. for 23.5 h. The solution was added to ice with CHCl3 and H2O, and the aqueous layer was extracted with CHCl3 (2×). The combined extracts were washed with 75 mL of saturated NaHCO3 solution, and the aqueous layer was extracted with CHCl3. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to give 2.3 g of 2,6-dimethyl-4-nitropyridine 1-oxide in 76% yield which was used without further purification.

Workup

  1. extractionthe aqueous layer was extracted with CHCl3 (2×)
  2. washThe combined extracts were washed with 75 mL of saturated NaHCO3 solution
  3. extractionthe aqueous layer was extracted with CHCl3
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7294282d81874981a4d8835a09f100bd
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Linked notes

Loading…