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

HRID 371620Notes

Reaction equation

HRID 371620 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].[NH2:14][NH2:15].C(=O)([O-])[O-].[Na+].[Na+].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:14][NH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 10340Sodium CarbonateHCID 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 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a reaction flask was added 26.1 grams (0.1 mole) of tetrachloropicolinic acid, 200 milliliters of water, 3.6 grams of 95 percent hydrazine (0.11 mole) and 10.6 grams (0.1 mole) of sodium carbonate. The mixture was heated with stirring and maintained under reflux conditions for about 1 hour. The reaction mixture was cooled to 25° C and 25 milliliters of 5 normal hydrochloric acid was added. The solid which precipitated was recovered by filtration, and washed successively with water, ethanol, benzene and hexane and air dried. The 3,5,6-trichloro-4-hydrazinopicolinic acid product was recovered in a yield of 25.6 grams (93 percent of theoretical) having a melting point of 165°-170° C. After recrystallization from a 50:50 dimethylformamide-water mixture the product (as the mono-hydrate) was found by analysis to have carbon, hydrogen and nitrogen contents of 26.6, 2.1 and 15.3 percent, respectively, as compared with the theoretical contents of 26.2, 2.2 and 15.3 percent, respectively, calculated for the above named compound.

Workup

  1. temperatureThe mixture was heated
  2. temperaturemaintained under reflux conditions for about 1 hour
  3. customThe solid which precipitated
  4. filtrationwas recovered by filtration
  5. washwashed successively with water, ethanol, benzene and hexane and air
  6. customdried
  7. customThe 3,5,6-trichloro-4-hydrazinopicolinic acid product was recovered in a yield of 25.6 grams (93 percent of theoretical)
  8. customAfter recrystallization from a 50:50 dimethylformamide-water mixture the product (as the mono-hydrate)

Sources & evidence

ORD record
ord-d690ccfa2b3c43e1be98c68826743680
Source dataset
uspto-grants-1978_05
Patent number
US04087431

Reaction notes

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