Phenylhydrazine → 2-(Phenylhydrazino)succinonitrile

HRID 2287650Notes

Reaction equation

HRID 2287650 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](#[N:14])/[CH:10]=[CH:11]/[C:12]#[N:13]>>[C:1]1([NH:7][NH:8][CH:11]([CH2:10][C:9]#[N:14])[C:12]#[N:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7516Phenylhydrazine2×HCID 637930Fumaronitrile

Product 1

HCID 538654852-(Phenylhydrazino)succinonitrileYield 45%

Conditions

Temperature
77.5 °C

Procedure

A mixture of phenylhydrazine (4.29 g) and fumaronitrile (3.1 g), where the phenylhydrazine served as a solvent, was heated at 75-80° C. for 20 hours. Purification by flash chromatography on silica gel and crystallization from dichloromethane/hexane gave the title compound (3.29 g, 45%), m.p. 97-98° C.

Workup

  1. customPurification by flash chromatography
  2. customon silica gel and crystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-57ed25fe42394ac3800c88b2fe3542ff
Source dataset
uspto-grants-2000_07
Patent number
US06084105

Reaction notes

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