Nitric Acid → Pyridine, 2,5-dimethyl-4-nitro-, 1-oxide

HRID 2207661Notes

Reaction equation

HRID 2207661 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N+:12]=1[O-:18].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:10][C:11]1[CH:16]=[C:15]([N+:6]([O-:9])=[O:7])[C:14]([CH3:17])=[CH:13][N+:12]=1[O-:18]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 5717732,5-Dimethylpyridin-1-ium-1-olate

Product 1

HCID 146707Pyridine, 2,5-dimethyl-4-nitro-, 1-oxideYield 85.4%

Conditions

Temperature
0 °C

Procedure

To a nitrating mixture of sulphuric acid (24 mL) and nitric acid (12 mL) cooled to 0° C. was added 2,5-dimethyl-1-oxido-pyridin-1-ium (CAS: 4986-05-4) (8.4 g, 68.21 mmol). The solution was allowed to warm to room temperature and stirred over 30 mins then heated to 110° C. and stirred over 5 hrs. The reaction mixture was cooled and poured onto ice. The aqueous solution was made basic with solid sodium carbonate, giving a precipitate. The aqueous was extracted into DCM (3x), and the combined extracts were dried over magnesium sulphate, filtered and evaporated to yield a yellow solid, 2,5-dimethyl-4-nitro-1-oxido-pyridin-1-ium (D135) (9.8 g, 58.3 mmol, 85.4% yield);

Workup

  1. temperatureto warm to room temperature
  2. temperaturethen heated to 110° C.
  3. stirringstirred over 5 hrs
  4. temperatureThe reaction mixture was cooled
  5. additionpoured onto ice
  6. customgiving a precipitate
  7. extractionThe aqueous was extracted into DCM (3x)
  8. dry with materialthe combined extracts were dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-d21db06608b14e10a3d858918035eac9
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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