Sodium Hydroxide → HCID 19791114, compound

HRID 1655234Notes

Reaction equation

HRID 1655234 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[C:12]([CH3:13])=[C:11]([N+]([O-])=O)[C:10]([F:17])=[CH:9][N:8]=1.[OH-:18].[Na+]>ClCCl>[CH3:6][C:7]1[C:12]([CH3:13])=[C:11]([Cl:3])[C:10]([F:17])=[CH:9][N+:8]=1[O-:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 19791177HCID 19791177, compound

Product 1

HCID 19791114HCID 19791114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phosphoryl chloride (8.6 ml) in dichloromethane (50 ml) was added to a stirred solution of 2,3-dimethyl-4-nitro-5-fluoropyridine (5.8 g) in dichloromethane (100 ml). The reaction mixture was heated under reflux for 4 hours. After cooling and pouring onto ice, the mixture was basified (NaOH) to pH 12 and extracted with dichloromethane. After drying (K2CO3) and removal of solvent, the crude product was purified by column chromatography (silica gel, 2%MeOH/CHCl3) to give 2,3-dimethyl-4-chloro-5-fluoropyridine-N-oxide (4.11 g) m.p. 137°-39°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. additionpouring onto ice
  5. extractionextracted with dichloromethane
  6. customAfter drying
  7. custom(K2CO3) and removal of solvent
  8. customthe crude product was purified by column chromatography (silica gel, 2%MeOH/CHCl3)

Sources & evidence

ORD record
ord-d4a572731ed5412ea8d5a6e1abd42f15
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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