Hydrazine → 1-(3-Chloro-4-p-tolylpyridin-2-yl)hydrazine

HRID 2101275Notes

Reaction equation

HRID 2101275 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:16][NH2:17]>C1COCC1>[Cl:8][C:7]1[C:2]([NH:16][NH2:17])=[N:3][CH:4]=[CH:5][C:6]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 577994252,3-Dichloro-4-(4-methylphenyl)pyridine

Product 1

HCID 577993761-(3-Chloro-4-p-tolylpyridin-2-yl)hydrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2,3-dichloro-4-p-tolylpyridine (711 mg, 3.0 mmol) in THF (5 mL) at room temperature under argon was added hydrazine (288 mg, 9.0 mmol). The reaction mixture was heated at 60° C. under argon for 5 h. Analysis by HPLC/MS indicated that starting material had been consumed. After cooling the reaction mixture to room temperature, most of the solvent was removed under reduced pressure. Water (25 mL) was added to the residue while stirring. Solid precipitate was collected by filtration and further washed with water (15 mL×2). After drying in a vacuum oven under reduced pressure overnight, 692 mg of nearly pure title compound was obtained as an off-white solid. HPLC/MS: retention time=2.10 min, [M+H]+=234.

Workup

  1. customhad been consumed
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. custommost of the solvent was removed under reduced pressure
  4. additionWater (25 mL) was added to the residue
  5. filtrationSolid precipitate was collected by filtration
  6. washfurther washed with water (15 mL×2)
  7. dry with materialAfter drying in a vacuum oven under reduced pressure overnight, 692 mg of nearly pure title compound
  8. customwas obtained as an off-white solid

Sources & evidence

ORD record
ord-d3d7eb0ea8e249f5bfc6a647d89c6d43
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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