Acrylonitrile → 3-(2-Methylamino-phenoxy)-propionitrile

HRID 1848661Notes

Reaction equation

HRID 1848661 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[C:10](#[N:13])[CH:11]=[CH2:12]>O.C(OCC)(=O)C>[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:12][CH2:11][C:10]#[N:13]

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 69138o-(Methylamino)phenol

Product 1

HCID 686026273-(2-Methylamino-phenoxy)-propionitrileYield 378.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methylaminophenol (0.74 g, 6.0 mmol), Triton B (60 μL, 40% in water) and acrylonitrile (4.0 mL, 60 mmol) was refluxed for 16 hrs. The mixture was diluted with ethyl acetate. The organic layer was then washed with water and brine, and was dried over MgSO4. After filtration and concentration, the residue was purfied via silica gel flash column chromatography eluting with 20% ethyl acetate in hexane to give 3-(2-methylamino-phenoxy)-propionitrile (4.0 g) as a brown oil. [M+H]+177.1; tR=0.715 min (method 1).

Workup

  1. washThe organic layer was then washed with water and brine
  2. dry with materialwas dried over MgSO4
  3. filtrationAfter filtration and concentration
  4. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2301c34652904bb9ace6767be368d3f4
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

Loading…