Triethylamine → 2-Pyridinecarbonitrile, 3,5,6-trichloro-4-hydrazino-

HRID 918454Notes

Reaction equation

HRID 918454 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([Cl:10])=[C:4](Cl)[C:3]=1[Cl:12].[NH2:13][NH2:14].C(N(CC)CC)C>C(O)C>[Cl:10][C:5]1[C:6]([C:8]#[N:9])=[N:7][C:2]([Cl:1])=[C:3]([Cl:12])[C:4]=1[NH:13][NH2:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9321HydrazineHCID 87323Tetrachloropicolinonitrile

Product 1

HCID 18986162-Pyridinecarbonitrile, 3,5,6-trichloro-4-hydrazino-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a reaction flask was added 400 milliliters of 95 percent ethanol and 24.2 grams (0.10 mole) of tetrachloropicolinonitrile. The mixture was heated to 45°C. with stirring and 3.7 grams (0.11 mole) of 95 percent hydrazine and 10.1 grams (0.10 mole) of triethylamine was added thereto. The mixture was heated under reflux for 1 hour and the reaction mixture thereafter cooled to 40°C. To this mixture was added 400 grams of an ice-water mixture and the solid 3,5,6-trichloro-4-hydrazinopicolinonitrile product which precipitated was recovered by filtration, water washed and dried. The product was recovered in a yield of 20.6 grams (87 percent of theoretical) melting at 178°-181°C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethe reaction mixture thereafter cooled to 40°C
  4. customthe solid 3,5,6-trichloro-4-hydrazinopicolinonitrile product which precipitated
  5. filtrationwas recovered by filtration, water
  6. washwashed
  7. customdried
  8. customThe product was recovered in a yield of 20.6 grams (87 percent of theoretical) melting at 178°-181°C.

Sources & evidence

ORD record
ord-fb55d85b9c0041418a4190ef1d12f21a
Source dataset
uspto-grants-1976_07
Patent number
US03971799

Reaction notes

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