Hydrazine hydrate (1:1) → 3-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine

HRID 1109442Notes

Reaction equation

HRID 1109442 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1>C(O)C>[Cl:11][C:10]1[C:5]([NH:2][NH2:3])=[N:6][CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 12726913-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 60 mL of hydrazine monohydrate in 380 mL of ethanol was added 81 g (0.38 mole) of 2,3-dichloro-5-trifluoromethylpyridine during a period of 25 minutes. At the end of the addition the temperature had risen to 37° C. This mixture was heated to reflux and maintained at reflux for approximately 15 hours. The solvent was evaporated under reduced pressure, leaving a wet slurry that was immediately recrystallized from boiling ethanol/water (5:2). The mixture was cooled to 20° C. and then filtered. The filter cake was air-dried, yielding approximately 60 g of 3-chloro-5-trifluoromethylpyrid-2-ylhydrazine. The NMR spectrum was consistent with the assigned structure. This reaction was repeated to obtain additional material for subsequent reactions.

Workup

  1. additionAt the end of the addition the temperature
  2. customhad risen to 37° C
  3. temperatureThis mixture was heated
  4. temperatureto reflux
  5. temperaturemaintained
  6. temperatureat reflux for approximately 15 hours
  7. customThe solvent was evaporated under reduced pressure
  8. customleaving a wet slurry that
  9. customwas immediately recrystallized
  10. filtrationfiltered
  11. customThe filter cake was air-dried

Sources & evidence

ORD record
ord-6c24d47e49874163aea2f2c19a41a24a
Source dataset
uspto-grants-1994_06
Patent number
US05321002

Reaction notes

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