Nitric Acid → Pyridine, 2-methyl-4-nitro-, 1-oxide

HRID 963475

Reaction equation

HRID 963475 reaction equation
S(=O)(=O)(O)O.[N+:6]1([O-:13])[C:7]([CH3:12])=[CH:8][CH:9]=[CH:10][CH:11]=1.[N+:14]([O-])([OH:16])=[O:15].[OH-].[Na+]>O>[N+:14]([C:9]1[CH:8]=[C:7]([CH3:12])[N+:6]([O-:13])=[CH:11][CH:10]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 136022-Methylpyridine 1-oxideHCID 14798Sodium Hydroxide

Product 1

HCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

98% sulfuric acid (17.5 ml) was added dropwise to 2-picoline-1-oxide (5.22 g) under stirring at cooling in an ice-bath. To the mixture was added dropwise nitric acid (fuming, 15 ml) under the same condition. After completion of the additieon, the mixture was heated at 80°-90° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, poured into water (100 ml) and alkalined with aN aqueous sodium hydroxide. The resultant mixture was extracted with chloroform four times. The combined extracts were dried over sodium sulfate. Removal of the solvent gave 4-nitro-2-picoline-1-oxide (6.52 g).

Workup

  1. temperatureat cooling in an ice-bath
  2. temperatureAfter completion of the additieon, the mixture was heated at 80°-90° C. for 2 hours
  3. extractionThe resultant mixture was extracted with chloroform four times
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-074ed863a1614baca9f8a10afa12ac57
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Linked notes

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