3-Phenylprop-2-enenitrile → HCID 20228193, compound

HRID 1731670Notes

Reaction equation

HRID 1731670 reaction equation
[Na].[NH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[NH2:3].[C:10](#[N:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[NH2:19][C:10]1[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)[N:3]=1

Participants

5

Reactant 3

HCID 746673-Phenylprop-2-enenitrileHCID 786452-HydrazinopyridineHCID 5360545Sodium

Product 1

HCID 20228193HCID 20228193, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.02 g. amount of sodium metal is dissolved in 250 ml. of absolute ethanol, then 21.82 g. of 2-hydrazinopyridine is added, followed by 25.8 g. of cinnamonitrile. The reaction mixture is refluxed for 16 hours, then the solvent is removed in vacuo. Water is added and the solid is collected by filtration. The solid is recrystallized from 3A ethanol to yield 20.32 g. of the desired product as yellow crystals, m.p. 203°-206° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. customthe solvent is removed in vacuo
  3. additionWater is added
  4. filtrationthe solid is collected by filtration
  5. customThe solid is recrystallized from 3A ethanol
  6. customto yield 20.32 g

Sources & evidence

ORD record
ord-2f260835f7be463ab968e6b22ca8aec8
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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