Potassium Carbonate → 2-Chloro-6-methyl-4-nitropyridine

HRID 333070Notes

Reaction equation

HRID 333070 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[N+:3]=1[O-].P(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24387Phosphorus trichlorideHCID 27518132-Chloro-6-methyl-4-nitropyridin-N-oxide

Product 1

HCID 2986072-Chloro-6-methyl-4-nitropyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Chloro-4-nitro-6-methyl-pyridine 1-oxide (6.2 g, 0.033 mol) was dissolved in chloroform (100 ml), phosphorus trichloride was added (22.6 g, 0.165 mol) and the mixture was heated under reflux for 2 days. The mixture was cooled to room temperature, poured into icewater and the mixture was neutralized with solid potassium carbonate. The phases were separated, the aqueous phase was extracted three times with chloroform, the combined organic phases were dried over magnesium sulfate. The solvent was removed under reduced pressure after which 5.326 g of a brown oil was obtained (0.031 mol, 94%) which was used directly in the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 days
  3. additionpoured into icewater
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted three times with chloroform
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure after which 5.326 g of a brown oil
  8. customwas obtained (0.031 mol, 94%) which

Sources & evidence

ORD record
ord-24932a00954f403ea0716094da62e798
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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