Potassium Carbonate → 2-(3-Aminophenoxy)acetonitrile

HRID 2205920Notes

Reaction equation

HRID 2205920 reaction equation
Br[CH2:2][C:3]#[N:4].[NH2:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[NH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[O:12][CH2:2][C:3]#[N:4]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 115683-Aminophenol

Product 1

HCID 187896992-(3-Aminophenoxy)acetonitrileYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromoacetonitrile (0.22 g, 1.83 mmol), 3-aminophenol (0.2 g, 1.83 mmol) and potassium carbonate (0.5 g, 3.67 mmol) were combined in dry DMF (10 ml). The reaction was stirred at room temperature for 24 hours. The reaction was diluted with water and ethyl acetate. The organic solution was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 50% ethyl acetate in dichloromethane to afford the title compound as a colourless oil (0.16 g, 58.9%). 1H-NMR (500 MHz, CDCl3): δ 3.76 (s, br, 2H), 4.69 (s, 2H), 6.29 (d, J=2.3 Hz, 1H), 6.37 (dd, J=2.3 Hz, 8.1 Hz, 1H), 6.41 (dd, J=2.3 Hz, 8.1 Hz, 1H), 7.1 (t, J=8.1 Hz, 1H).

Workup

  1. washThe organic solution was washed with brine
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel column chromatography
  5. washeluting with 50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-cfca4024562d4040bce16078fd341cc9
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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