Hydrochloric Acid → 3,5,6-Trichloro-4-hydrazinylpyridine-2-carboxylic acid

HRID 371621Notes

Reaction equation

HRID 371621 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([Cl:11])=[C:4](Cl)[C:3]=1[Cl:13].[OH-].[Na+].[NH2:16][NH2:17].Cl>O>[Cl:11][C:5]1[C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]([Cl:1])=[C:3]([Cl:13])[C:4]=1[NH:16][NH2:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14798Sodium Hydroxide2×HCID 826463,4,5,6-Tetrachloropyridine-2-carboxylic acid

Product 1

HCID 13834393,5,6-Trichloro-4-hydrazinylpyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a reaction flask containing 200 milliliters of water at the boiling point was added 26.1 grams (0.1 mole) of tetrachloropicolinic acid, 4.1 grams (0.103 mole) of sodium hydroxide in 25 milliliters of water and 3.47 grams (0.105 mole) of hydrazine. The reaction mixture was stirred under reflux for 30 minutes. An additional 4.1 grams (0.103 mole) of sodium hydroxide in 25 milliliters of water was slowly added to the reaction mixture over a 25 minute period and the mixture refluxed for 45 minutes. The reaction mixture was cooled to room temperature and 25 milliliters of 5 Normal hydrochloric acid was added thereto. The solid 3,5,6-trichloro-4-hydrazinopicolinic acid (as the mono-hydrate), which precipitated was recovered by filtration in a yield of 22.9 grams (83.5 percent of theoretical) and melted at 166°-168° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperaturethe mixture refluxed for 45 minutes
  3. customThe solid 3,5,6-trichloro-4-hydrazinopicolinic acid (as the mono-hydrate), which precipitated
  4. filtrationwas recovered by filtration in a yield of 22.9 grams (83.5 percent of theoretical) and melted at 166°-168° C.

Sources & evidence

ORD record
ord-99ffd6b28e574d088b7d97236a7623d7
Source dataset
uspto-grants-1978_05
Patent number
US04087431

Reaction notes

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