3-(4-Nitrophenyl)propionitrile → 10139-91-0

HRID 1725714Notes

Reaction equation

HRID 1725714 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]#[N:13])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]#[N:13])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 50518053-(4-Nitrophenyl)propionitrile

Product 1

HCID 1041932410139-91-0Yield 84.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(4-Nitrophenyl)propionitrile (740 mg, 4.2 mmol) was dissolved in methanol (100 mL), 10% Pd/C was added and the mixture was shaken under a hydrogen atmosphere (50 psi) at room temperature for 30 minutes. The mixture was filtered through Celite, and washed with 20 mL of methanol. The combined organic solvent was concentrated under reduced pressure to give crude materials which was further purified by flash column chromatography (Ethyl acetate:Hexanes 1:1) to yield 520 mg of 3-(4-Aminophenyl)propionitrile as a light yellow oil. 1H NMR (DMSO-d6): δ 6.91-6.88 (d, J=9.0 Hz, 2H), 6.49-6.46 (d, J=9.0 Hz, 2H), 4.92 (s, 2H), 2.66 (s, 4H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with 20 mL of methanol
  3. concentrationThe combined organic solvent was concentrated under reduced pressure
  4. customto give crude materials which
  5. customwas further purified by flash column chromatography (Ethyl acetate:Hexanes 1:1)

Sources & evidence

ORD record
ord-0cae550636d04ad682d11bf2299b3d04
Source dataset
uspto-grants-2009_02
Patent number
US07491732B2

Reaction notes

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