3-Nitrophenylacetonitrile → (3-Amino-phenyl)-acetonitrile

HRID 1749482Notes

Reaction equation

HRID 1749482 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl-].N>CCO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 121253-NitrophenylacetonitrileHCID 20976574Ammonia chloride

Product 1

HCID 4847850(3-Amino-phenyl)-acetonitrileYield 96.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (3-nitro-phenyl)-acetonitrile (2.00 g, 12.35 mmol), iron dust (2.07 g, 37.03 mmol) and ammonia chloride (1.96 g, 37.03 mmol) in EtOH (20 mL) and water (4 mL) was refluxed at 85° C. for 1 h. The reaction mixture was filtered through cellite and rinsed with EtOH. The combined filtrate was concentrated and the residue was purified by silica gel column chromatography (20% ethyl acetate in petroleum ether) to afford the title compound (1.57 g, 11.89 mmol, 96% yield) as a pale-yellow solid. MS (ESI) m/z 133.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through cellite
  2. washrinsed with EtOH
  3. concentrationThe combined filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-1d9bf41c61664ff0b9ff0ccb5dabf58e
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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