Hydrazine → 2-Hydrazinyl-5-iodopyridine

HRID 1372465Notes

Reaction equation

HRID 1372465 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[NH2:9][NH2:10]>N1C=CC=CC=1>[I:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][NH2:10])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 223971882-Hydrazinyl-5-iodopyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-chloro-5-iodopyridine (1.918 g, 8.01 mmol), anhydrous hydrazine (1.26 mL, 40.05 mmol) and pyridine (30 mL) was warmed at reflux for 18 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between dichloromethane and 1N aqueous sodium hydroxide solution. The organic layer was separated, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was triturated with hexanes, and the resultant precipitate was collected and dried in vacuo to afford the title compound as off-white crystals. LC/MS 235.8 (M+1).

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 18 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was partitioned between dichloromethane and 1N aqueous sodium hydroxide solution
  5. customThe organic layer was separated
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with hexanes
  9. customthe resultant precipitate was collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-bea3ef6a301e4f3685fe133979457d6b
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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