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

Participants

Reaction Steps

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.

Provenance & Evidence