Ethyl Acetate → 1-(4-Aminophenyl)cyclopropanecarbonitrile

HRID 2408500Notes

Reaction equation

HRID 2408500 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.CCOC(C)=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:13]#[N:14])[CH2:11][CH2:12]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 43990411-(4-Nitrophenyl)cyclopropanecarbonitrile

Product 1

HCID 138269361-(4-Aminophenyl)cyclopropanecarbonitrileYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(4-nitro-phenyl)-cyclopropanecarbonitrile (500 mg, 2.65 mmol, Journal of the American Chemical Society, 71, 2031-5; 1949) in 7 mL of EtOH-2.5 mL of EtOAc was added 350 mg 5% Pd—C. The mixture was stirred under 1 atm of H2 overnight. The reaction was filtered, concentrated in vacuo and then purified using preparative thin layer chromatography (CHCl3) to afford the title compound as an oil (96 mg, 23%). Mass spectrum (ESI, m/z): Cald. C10H10N2, 159.0, found 159.2.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-0d2e14a5b5a640e287d56d7cfcf17e41
Source dataset
uspto-grants-2014_08
Patent number
US08815867B2

Reaction notes

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