Hydrazine hydrate (1:1) → 2-Chloro-6-hydrazinyl-3-(trifluoromethyl)pyridine

HRID 1961695Notes

Reaction equation

HRID 1961695 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[C:4]([Cl:12])[N:3]=1.O.[NH2:14][NH2:15]>C(O)C>[Cl:12][C:4]1[N:3]=[C:2]([NH:14][NH2:15])[CH:7]=[CH:6][C:5]=1[C:8]([F:11])([F:10])[F:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18103372,6-Dichloro-3-(trifluoromethyl)pyridine

Product 1

HCID 582302262-Chloro-6-hydrazinyl-3-(trifluoromethyl)pyridineYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2,6-Dichloro-5-trifluoromethyl-pyridine (18, 2 g, 9.26 mmol) in ethanol (30 mL) was added hydrazine hydrate (2.9 g, 46 mmol). The reaction mixture was stirred for 4 h at room temperature, then concentrated to remove the solvent, and added ethyl acetate, washed with water. The organic layer was dried over anhydrous Na2SO4. Column chromatography (Silica, petroleum ether/ethyl acetate=4/1˜3/1) afforded compound 19 as white solid (yield: 56%) and another isomer 20 (yield: 18%).

Workup

  1. concentrationconcentrated
  2. customto remove the solvent
  3. additionadded ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-31422a61ac634120b1b88df44cf3016e
Source dataset
uspto-grants-2013_04
Patent number
US08415357B2

Reaction notes

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