Nitric Acid → 2-Chloro-5-methyl-4-nitropyridine N-oxide

HRID 271066Notes

Reaction equation

HRID 271066 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N+:7]=1[O-:13].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[Cl:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:4])=[O:2])[C:9]([CH3:12])=[CH:8][N+:7]=1[O-:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 134316232-Chloro-5-methylpyridin-1-ium-1-olate

Product 1

HCID 123180102-Chloro-5-methyl-4-nitropyridine N-oxideYield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 165 mL of nitric acid and 209 mL of sulfuric acid was slowly added 56.4 g of 2-chloro-5-methylpyridine-1-oxide. The reaction mixture was stirred at 100° C. for two hours, cooled to room temperature, and added to ice. Sodium carbonate was added to adjust the pH to about pH 2 to pH 3. The resulting yellow solid was separated by filtration and washed with ice-water. The combined filtrates were extracted with hot chloroform. The extracts were combined, dried over sodium sulfate, and concentrated to give 59.1 g of 2-chloro-5-methyl-4-nitropyridine-1-oxide (80%). Mass Spec. M+H=189.

Workup

  1. temperaturecooled to room temperature
  2. additionadded to ice
  3. customThe resulting yellow solid was separated by filtration
  4. washwashed with ice-water
  5. extractionThe combined filtrates were extracted with hot chloroform
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-714a8f5a8b6f4df6a42c8845c85d676a
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Reaction notes

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