Propanenitrile, 3-ethoxy- → 3-Amino-1-m-tolyl-2-pyrazoline

HRID 2198982

Reaction equation

HRID 2198982 reaction equation
[Na].Cl.[C:3]1([CH3:11])[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][NH2:10])[CH:4]=1.C(O[CH2:15][CH2:16][C:17]#[N:18])C>C(O)C>[NH2:18][C:17]1[CH2:16][CH2:15][N:9]([C:5]2[CH:4]=[C:3]([CH3:11])[CH:8]=[CH:7][CH:6]=2)[N:10]=1

Participants

5

Reactant 3

HCID 16501Propanenitrile, 3-ethoxy-HCID 71562m-Tolylhydrazinium(1+) chlorideHCID 5360545Sodium

Product 1

HCID 23264163-Amino-1-m-tolyl-2-pyrazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.8 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 15.8 g. of m-tolylhydrazine hydrochloride is added followed in 5 minutes by 9.9 g. of β-ethoxypropionitrile. The reaction mixture is refluxed for 16 hours, then is evaporated to dryness in vacuo. Water is added and the precipitate is collected by filtration. The solid is dissolved in dichloromethane and is passed through a short column of a hydrous magnesium silicate. The column effluent is refluxed on a steam bath with the gradual addition of hexane to crystallize a product. The mixture is cooled and filtered to give 10.1 g. of the product of the Example as colorless crystals, m.p. 119°-120° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. customis evaporated to dryness in vacuo
  3. additionWater is added
  4. filtrationthe precipitate is collected by filtration
  5. dissolutionThe solid is dissolved in dichloromethane
  6. temperatureThe column effluent is refluxed on a steam bath with the gradual addition of hexane
  7. customto crystallize a product
  8. temperatureThe mixture is cooled
  9. filtrationfiltered
  10. customto give 10.1 g

Sources & evidence

ORD record
ord-1889e131314a447f97a082c35398c27d
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Linked notes

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