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

HRID 1266934Notes

Reaction equation

HRID 1266934 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.O.[NH2:14][NH2:15]>C(O)C>[Cl:8][C:7]1[C:2]([NH:14][NH2:15])=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=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)pyridineYield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction flask was loaded with 2,3-dichloro-5-trifluoromethylpyridine (15 g) and ethanol (90 ml), followed by dropwise addition of hydrazine monohydrate (10.4 g) to the flask in one hour with stirring. After stirring overnight, the reaction mixture was filtrated, and the filtrate was condensed to precipitate crystals. The crystals were filtrated for collection and air-dried to give 3-chloro-2-hydrazino-5-trifluoromethylpyridine (9.1 g).

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe reaction mixture was filtrated
  3. customcondensed
  4. customto precipitate crystals
  5. filtrationThe crystals were filtrated for collection
  6. customair-dried

Sources & evidence

ORD record
ord-b42fe837f20d43b1b3e0f17c45bad85e
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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