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

HRID 448949Notes

Reaction equation

HRID 448949 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 purified 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. customthe residue was purified via silica gel flash column chromatography
  5. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3b4db32a37024de9a015922a66821a15
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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