Methylhydrazine → 2-(1-Methylhydrazinyl)-5-(trifluoromethyl)pyridine

HRID 355605Notes

Reaction equation

HRID 355605 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH3:12][NH:13][NH2:14].[OH-].[Na+]>>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:13]([CH3:12])[NH2:14])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 6061MethylhydrazineHCID 14798Sodium HydroxideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 27777822-(1-Methylhydrazinyl)-5-(trifluoromethyl)pyridine

Conditions

Temperature
90 °C

Procedure

2-Chloro-5-trifluoromethylpyridine (44.3 g; 0.24 mol) was treated with several portions of methyl hydrazine (33.9 g; 0.74 mol) at room temperature under nitrogen. The mixture was heated at 90° C. for 6 hr. The resulting solid was treated with 3M aqueous NaOH and extracted with ethyl acetate. The organic extracts were dried and evaporated to leave an oil/solid. Distillation of the crude product to remove excess hydrazine gave 1-[5-trifluoromethylpyrid-2-yl]-1-methyl hydrazine as a white solid (44.0 g; 94%), m.pt. 52°-55° C. ##STR14##

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic extracts were dried
  3. customevaporated
  4. customto leave an oil/solid
  5. distillationDistillation of the crude product
  6. customto remove excess hydrazine

Sources & evidence

ORD record
ord-2eedafe9be9a4ae888b53024aeb5ce02
Source dataset
uspto-grants-1998_11
Patent number
US05833885

Reaction notes

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