Nitric Acid → HCID 67280656, compound

HRID 1693335Notes

Reaction equation

HRID 1693335 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[N+:4]([O-:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N+:11]([O-])([OH:13])=[O:12].C(=O)([O-])[O-].[NH4+].[NH4+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([CH3:10])=[N+:4]([O-:9])[CH:5]=[C:6]([CH3:8])[C:7]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 517111Ammonium CarbonateHCID 67279710Pyridine, 3-chloro-2,5-dimethyl-, 1-oxide

Product 1

HCID 67280656HCID 67280656, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

The above 3-chloro-2,5-dimethylpyridine 1-oxide (1.20 g) was dissolved in concentrated sulfuric acid (6 mL), and a mixture of fuming nitric acid (9.5 mL) and fuming sulfuric acid (5.5 mL) was added dropwise over 25 minutes. After stirring in that state for 30 minutes, the mixture was stirred at 90° C. for two hours. The reaction solution was left to cool, and then introduced into ice water and neutralized with ammonium carbonate with stirring at room temperature. The insoluble matter was separated off by filtration, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (1.11 g, 72%) as a solid.

Workup

  1. additionwas added dropwise over 25 minutes
  2. stirringthe mixture was stirred at 90° C. for two hours
  3. waitThe reaction solution was left
  4. temperatureto cool
  5. stirringwith stirring at room temperature
  6. customThe insoluble matter was separated off by filtration
  7. extractionfollowed by extraction with chloroform
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-e89e2b43688d44008dc6b8f190574a68
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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