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

HRID 1962268Notes

Reaction equation

HRID 1962268 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-1fdda2cf087e46ecaeab0e22f23a355a
Source dataset
uspto-grants-2013_04
Patent number
US08415365B2

Reaction notes

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