Nitric Acid → 2-methyl-3-fluoro-4-nitropyridine-N-oxide

HRID 1655226Notes

Reaction equation

HRID 1655226 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[N+:10]([O-:13])(O)=[O:11].[CH3:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N+:16]=1[O-:22].C(=O)([O-])[O-].[NH4+].[NH4+]>S(=O)(=O)(O)O>[CH3:14][C:15]1[C:20]([F:21])=[C:19]([N+:10]([O-:13])=[O:11])[CH:18]=[CH:17][N+:16]=1[O-:22]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 24681Fuming sulfuric acidHCID 517111Ammonium CarbonateHCID 197911603-Fluoro-2-methylpyridine 1-oxide

Product 1

HCID 197911692-methyl-3-fluoro-4-nitropyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A nitration mixture of 30% oleum (55 ml) and fuming nitric acid (90 ml) was added dropwise with cooling and stirring to a solution of 2-methyl-3-fluoropyridine-N-oxide (13.3 g) in concentrated sulphuric acid (48 ml) at 10°-15°. The solution was stirred at room temperature for 1.5 hours and then for 2 hours at 100°. After cooling, the mixture was poured onto ice, basified (ammonium carbonate) and extracted with dichloromethane. After drying (K2CO3), the extracts were evaporated to dryness to give 2-methyl-3-fluoro-4-nitropyridine-N-oxide (12.12 g) m.p. 170°-175°.

Workup

  1. additionwas added dropwise
  2. temperaturewith cooling
  3. waitfor 2 hours at 100°
  4. temperatureAfter cooling
  5. additionthe mixture was poured onto ice
  6. extractionextracted with dichloromethane
  7. dry with materialAfter drying (K2CO3)
  8. customthe extracts were evaporated to dryness

Sources & evidence

ORD record
ord-8ca17b0a1f9d4c6e9b94c7539484d044
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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