Acrylonitrile → 3-(2-(2,5-Difluorophenyl)hydrazinyl)propanenitrile

HRID 1466576Notes

Reaction equation

HRID 1466576 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[F:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[NH:13][NH2:14]>C(O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[NH:13][NH:14][CH2:3][CH2:2][C:1]#[N:4]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 5889572,5-Difluorophenylhydrazine

Product 1

HCID 668471273-(2-(2,5-Difluorophenyl)hydrazinyl)propanenitrileYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of acrylonitrile (10 mL), ethanol (20 mL) and 2,5-difluorophenylhydrazine (790 mg) was heated to reflux for 2 days. The reaction was concentrated under vacuum and the product purified by flash chromatography on silica gel with methylene chloride to give 790 mg (73%) 3-(2-(2,5-difluorophenyl)hydrazinyl)propanenitrile. LCMS (ESI) m+H=198.2; 1H NMR (400 MHz, CDCl3) δ 6.99 (ddd, 1H), 6.89 (ddd, 1H), 6.38 (tt, 1H), 5.45 (s, 1H), 3.91 (s, 1H), 3.19 (td, 2H), 2.61 (t, 2H).

Workup

  1. temperatureto reflux for 2 days
  2. concentrationThe reaction was concentrated under vacuum
  3. customthe product purified by flash chromatography on silica gel with methylene chloride

Sources & evidence

ORD record
ord-77b54b45d60d4638839808b21314bb03
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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