Hydrazine hydrate (1:1) → 2-Hydrazinyl-3-iodo-4-methylpyridine

HRID 2096986Notes

Reaction equation

HRID 2096986 reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.O.[NH2:11][NH2:12]>N1C=CC=CC=1>[NH:11]([C:2]1[C:7]([I:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1)[NH2:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 451082072-Chloro-3-iodo-4-methylpyridine

Product 1

HCID 581543012-Hydrazinyl-3-iodo-4-methylpyridineYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-chloro-3-iodo-4-methylpyridine (preparation 28a, 2.0 g, 7.9 mmol) and hydrazine hydrate (1.2 mL, 24.2 mmol) in pyridine (12 mL) under an argon atmosphere was stirred and heated to reflux. After 24 hours, the mixture was cooled and evaporated to dryness. The crude mixture was triturated with water and the solid was filtered and washed with water to give the title compound (1.71 g, 87%) which was used without further purification in the next reaction.

Workup

  1. temperatureheated to reflux
  2. temperaturethe mixture was cooled
  3. customevaporated to dryness
  4. customThe crude mixture was triturated with water
  5. filtrationthe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-a29fe50d7b4c424f8c8843fbd62557c8
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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