Ammonium Hydroxide → 4-Chloro-2,3-dimethyl-5-nitropyridine

HRID 1988855Notes

Reaction equation

HRID 1988855 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](O)[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:15])=O.P(Cl)(Cl)(Cl)(Cl)Cl.[OH-].[NH4+]>>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:15])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178432967HCID 178432967, compound

Product 1

HCID 687048624-Chloro-2,3-dimethyl-5-nitropyridine

Procedure

2,3-Dimethyl-4-hydroxy-5-nitropyridine (26.8 g, 0.16 mol) prepared in Step 3 was added to 85 ml of phosphorus oxychloride. Phosphorus pentachloride (33.3 g, 0.16 mol) was added to the reaction mixture, which was then refluxed under stirring for 2 hours. The reaction mixture was left overnight at room temperature, added to ice water, brought to pH 5 with 28% ammonium hydroxide, and then extracted with ether. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated to give 28.3 g of the titled compound.

Workup

  1. temperaturewas then refluxed
  2. waitThe reaction mixture was left overnight at room temperature
  3. extractionextracted with ether
  4. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da856d17dfde4b5abf40514dfbf526e3
Source dataset
uspto-grants-2010_01
Patent number
US07642269B2

Reaction notes

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