Nitric Acid → 2,3-Dimethyl-4-nitropyridine-N-oxide

HRID 703158Notes

Reaction equation

HRID 703158 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:9].[N+:10]([O-])([OH:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:4][N+:3]=1[O-:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 3840573Pyridine, 2,3-dimethyl-, 1-oxide

Product 1

HCID 1482232,3-Dimethyl-4-nitropyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 183 mg of 2,3-dimethylpyridine 1-oxide in 0.6 ml of concentrated sulfuric acid was treated while cooling with ice with 0.2 ml of 65% nitric acid (d =1.4). The reaction mixture was stirred at 90° for 24 hours and poured on to a mixture of ice and sodium carbonate, whereupon the resulting mixture was extracted with methylene chloride and the methylene chloride phase was dried and evaporated. The residue, crystallized from ethanol/n-pentane, gave 2,3-dimethyl-4-nitropyridine 1-oxide of melting point 99-102°.

Workup

  1. extractionwas extracted with methylene chloride
  2. dry with materialthe methylene chloride phase was dried
  3. customevaporated
  4. customThe residue, crystallized from ethanol/n-pentane

Sources & evidence

ORD record
ord-d7c6e23c10c8478683c9f4b3a41d70c9
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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