Phosphorus oxychloride → 2-Chloro-5-methyl-3-nitropyridine

HRID 1943748Notes

Reaction equation

HRID 1943748 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](O)=[N:6][CH:7]=1.P(Cl)(Cl)([Cl:14])=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(#N)C>[Cl:14][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178430719HCID 178430719, compound

Product 1

HCID 8183002-Chloro-5-methyl-3-nitropyridineYield 97%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

5-methyl-3-nitro-pyridin-2-ol (5 g, 32.4 mmol) and benzyltrimethyl ammonium chloride (3.01 g, 16.2 mmol) were dissolved in acetonitrile, and phosphorus oxychloride (9.0 ml, 97.2 mmol) was added thereto and stirred at 800 for 6 hours. The reaction mixture was cooled and poured into ice water to quench the reaction, and extracted with dichloromethane. The combined organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane. The fractions containing the product were collected and evaporated to obtain 2-chloro-5-methyl-3-nitro-pyridine as yellow solid (5.39 g, 97%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto quench
  3. customthe reaction
  4. extractionextracted with dichloromethane
  5. washThe combined organic layer was washed with saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica eluting with a solvent of dichloromethane
  10. additionThe fractions containing the product
  11. customwere collected
  12. customevaporated

Sources & evidence

ORD record
ord-c2ff4a311979427c82e72970c4596d9b
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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