Nitric Acid → 2,3-dimethyl-4-nitro-5-fluoro-pyridine-N-oxide

HRID 1655233Notes

Reaction equation

HRID 1655233 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[N+:10]([O-:13])(O)=[O:11].[CH3:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([F:22])=[CH:17][N+:16]=1[O-:23].C(=O)([O-])[O-].[NH4+].[NH4+]>S(=O)(=O)(O)O>[CH3:14][C:15]1[C:20]([CH3:21])=[C:19]([N+:10]([O-:13])=[O:11])[C:18]([F:22])=[CH:17][N+:16]=1[O-:23]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 24681Fuming sulfuric acidHCID 517111Ammonium CarbonateHCID 197912325-Fluoro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 197912362,3-dimethyl-4-nitro-5-fluoro-pyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A nitration mixture of 30% oleum (24 ml) and fuming nitric acid (40 ml) was added dropwise with cooling to a solution of 2,3-dimethyl-5-fluoropyridine-N-oxide (6.64 g) in concentrated sulphuric acid (24 ml) at 10°-15°. The solution was stirred at room temperature for 1.5 hours and then 2 hours at 80°-90°. 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 2,3-dimethyl-4-nitro-5-fluoro-pyridine-N-oxide (5.88 g) m.p. 80°-83°.

Workup

  1. additionwas added dropwise
  2. custom2 hours
  3. customat 80°-90°
  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-f67d3f1296034ff293e2c97a3f0e1581
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

Loading…