Hydrazine → 2-Hydrazinyl-5-iodopyridine

HRID 1483858Notes

Reaction equation

HRID 1483858 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>[NH:9]([C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1)[NH2:10]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 223971882-Hydrazinyl-5-iodopyridineYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The solution of 2-chloro-5-iodopyridine (2.0 g, 20.9 mmol), anhydrous hydrazine (3.3 mL, 105 mmol) in pyridine (40 mL) was heated at reflux overnight. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added 1 N sodium hydroxide solution and it was extracted with EtOAc. The organic layer was separated, dried (sodium sulfate) and concentrated under reduced pressure. To the residue was added hexanes, and the precipitate was collected and dried in vacuo to afford the title compound (1.35 g, 69% yield) as off-white crystals. MS (ES+, m/z): 236.2 (M++1).

Workup

  1. temperatureat reflux overnight
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added 1 N sodium hydroxide solution and it
  4. extractionwas extracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. additionTo the residue was added hexanes
  9. customthe precipitate was collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-8d7be083a5264eb78a426ca3e534fcd2
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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