Water → 2-(3-Amino-2-pyrazolin-1-yl)pyridine

HRID 637320Notes

Reaction equation

HRID 637320 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[Na].[C:10](#[N:13])[CH:11]=[CH2:12].O>C(O)C>[NH2:13][C:10]1[CH2:11][CH2:12][N:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[N:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7855AcrylonitrileHCID 786452-HydrazinopyridineHCID 5360545Sodium

Product 1

HCID 134966252-(3-Amino-2-pyrazolin-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydrazinopyridine (0.545 g) was added to a solution of sodium (50 mg; 0.43 atoms) in dry absolute ethanol (2 ml) in a nitrogen atmosphere. Acrylonitrile (0.265 g; 0.32 ml; 1 mol) was added dropwise and the resulting solution heated for 4 hours on the steam bath. The reaction mixture was cooled, giving some crystals, and treated with water (10 ml) to give a suspension of a solid. The solid was collected and washed with water. Recrystallisation from ethanol (ca. 5 ml) gave the title compound m.p. 168°-169.5°. Thin Layer Chromatography: On Al2O3 in CHCl3 gave a single spot Rf 0.18.

Workup

  1. temperaturethe resulting solution heated for 4 hours on the steam bath
  2. temperatureThe reaction mixture was cooled
  3. customgiving some crystals
  4. customto give
  5. additiona suspension of a solid
  6. customThe solid was collected
  7. washwashed with water
  8. customRecrystallisation from ethanol (ca. 5 ml)

Sources & evidence

ORD record
ord-d632d654e44140898c53291ff8964800
Source dataset
uspto-grants-1985_12
Patent number
US04556671

Reaction notes

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