Nitric Acid → 2-Nitro-1-oxo-1lambda~5~-pyridine

HRID 1463191Notes

Reaction equation

HRID 1463191 reaction equation
OS(O)(=O)=O.C[C:7]1[C:12](C)=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:14].C([O-])([O-])=O.[Na+].[Na+].[N+:21]([O-])([OH:23])=[O:22]>>[N+:21]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N+:8]=1[O-:14])([O-:23])=[O:22]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 3840573Pyridine, 2,3-dimethyl-, 1-oxide

Product 1

HCID 124107812-Nitro-1-oxo-1lambda~5~-pyridine

Procedure

To 400 mL of concentrated H2SO4 was added slowly 130 g of impure 2,3-dimethylpyridine N-oxide. Fuming HNO3 (330 mL) was slowly added at a rate to keep the temperature between 120° C. and 170° C. After addition was complete, the temperature was held at 103° C. for 3 hours and then the reaction was cooled. The crude reaction was added to 1 kg ice in a large pan, then, with stirring, 1.1 kg Na2CO3 was added. After cooling to room temperature, the solids were removed by suction filtration from the solution. The filtrate was extracted with chloroform. The solids were washed with hot chloroform (3 times). The combined reduced organic extracts yielded 110 g of the crude desired nitropyridine N-oxide as an orange solid. ##STR8##

Workup

  1. customthe temperature between 120° C. and 170° C
  2. additionAfter addition
  3. temperaturethe reaction was cooled
  4. customThe crude reaction
  5. customthe solids were removed by suction filtration from the solution
  6. extractionThe filtrate was extracted with chloroform
  7. washThe solids were washed with hot chloroform (3 times)

Sources & evidence

ORD record
ord-f58f0f54bb9049bebd587d5835532b44
Source dataset
uspto-grants-1994_04
Patent number
US05300478

Reaction notes

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