Water → 2,3,6-Trichloropyridine

HRID 268312Notes

Reaction equation

HRID 268312 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[C:6](NN)[C:5]=1Cl.O>C(O)(C)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:11])=[C:8]([Cl:10])[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 125021922,3,5,6-Tetrachloro-4-hydrazinylpyridine

Product 1

HCID 230162,3,6-Trichloropyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 10 milliliter solution of 5 Normal sodium hydroxide was added a mixture of 5 grams of tetrachloro-4-hydrazinopyridine in 25 milliliters of isopropanol. The mixture was heated at its boiling point with rapid stirring for 2 hours. The mixture was mixed with 100 milliliters of water and the organic material extracted with methylene chloride. The organic phase was water washed and subjected to sublimation. The 2,5,6-trichloropyridine product was recovered in a yield of 1.85 grams (~ 51 percent of theoretical).

Workup

  1. temperatureThe mixture was heated at its
  2. extractionthe organic material extracted with methylene chloride
  3. washwashed
  4. customThe 2,5,6-trichloropyridine product was recovered in a yield of 1.85 grams (~ 51 percent of theoretical)

Sources & evidence

ORD record
ord-47bc4bbeec0d4b2788f882d54809bb18
Source dataset
uspto-grants-1976_03
Patent number
US03947457

Reaction notes

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