Hydrazine hydrate (1:1) → 2-Hydrazinyl-3-nitropyridine

HRID 1898805Notes

Reaction equation

HRID 1898805 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>CO>[NH:12]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[NH2:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 796132-Chloro-3-nitropyridine

Product 1

HCID 35789352-Hydrazinyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-3-nitropyridine (100 g, 0.63 mol), hydrazine monohydrate (70.4 mL, 72.6 g, 1.45 mol) and methanol (1.3 L) were mixed and heated to reflux with stirring. After 30 min the reaction mixture was cooled and filtered collecting the insoluble materials. The filtrate was concentrated by evaporation under reduced pressure and the residue obtained as well as the insoluble materials from the filtration were diluted with water. The insoluble solids present were collected by filtration, washed with water, and dried to obtain 95.2 g (98 percent of theory) of the title compound as a bright yellow powder melting at 168°-169° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureAfter 30 min the reaction mixture was cooled
  4. filtrationfiltered
  5. customcollecting the insoluble materials
  6. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  7. customthe residue obtained as well as the insoluble materials
  8. filtrationfrom the filtration
  9. additionwere diluted with water
  10. filtrationThe insoluble solids present were collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-7b08a32fb0614a88af1f9257025383d3
Source dataset
uspto-grants-1996_11
Patent number
US05571775

Reaction notes

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