3-Phenylprop-2-enenitrile → HCID 20228190, compound

HRID 1731667Notes

Reaction equation

HRID 1731667 reaction equation
[Na].[NH2:2][C:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]=2)[N:4]=1.C(#N)C=C[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[NH2:2][C:3]1[CH2:7][CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 746673-Phenylprop-2-enenitrileHCID 5360545SodiumHCID 202281833-Amino-1-(5-chloro-2-pyridyl)-2-pyrazoline

Product 1

HCID 20228190HCID 20228190, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.5 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 14.36 g. of 5-chloro-2-hydrazinopyridine (prepared as described in Example 3) is added followed by 12.92 g. of cinnamonitrile. The reaction mixture is refluxed for 16 hours. The solvent is removed in vacuo and water is added to the residue to separate a solid. The solid is collected by filtration and dissolved in dichloromethane. The solution is dried over anhydrous sodium sulfate and filtered through a hydrous magnesium silicate. The filtrate is concentrated while adding hexane to separate crystals. The material is recrystallized from ethyl acetate to give 11.68 g. of a light yellow crystalline material. The material is dried in vacuo to give the product of the Example as yellow crystals, m.p. 142°-147° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. customThe solvent is removed in vacuo and water
  3. additionis added to the residue
  4. customto separate a solid
  5. filtrationThe solid is collected by filtration
  6. dissolutiondissolved in dichloromethane
  7. dry with materialThe solution is dried over anhydrous sodium sulfate
  8. filtrationfiltered through a hydrous magnesium silicate
  9. concentrationThe filtrate is concentrated
  10. additionwhile adding hexane
  11. customto separate crystals
  12. customThe material is recrystallized from ethyl acetate
  13. customto give 11.68 g
  14. customThe material is dried in vacuo
  15. customto give the product of the Example as yellow crystals, m.p. 142°-147° C.

Sources & evidence

ORD record
ord-bad51592f5644cc69f2c8fa5e3c88fba
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

Loading…