1-(4-Nitrophenyl)cyclopentene → 4-Cyclopentylaniline

HRID 1465130Notes

Reaction equation

HRID 1465130 reaction equation
[C:1]1([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>CO.ClCCl.[Pd]>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH2:12])=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 1

HCID 593950631-(4-Nitrophenyl)cyclopentene

Product 1

HCID 118160214-CyclopentylanilineYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(1-Cyclopentenyl)-4-nitro-benzene (225 mg, 1.19 mmol) in methanol (10 mL) and dichloromethane (2.5 mL) was treated with 10% Pd/C (70 mg) and stirred under H2 atmosphere for 1 h at room temperature. The reaction was filtered and concentrated in vacuo to provide 4-cyclopentylaniline (180 mg, 94% yield). 1H NMR (400.0 MHz, MeOD) δ 7.01 (d, J=8.2 Hz, 2H), 6.73-6.70 (m, 2H), 2.88 (dd, J=2.3, 17.3 Hz, 1H), 2.00-1.95 (m, 2H), 1.80-1.75 (m, 2H), 1.70-1.64 (m, 2H), 1.56-1.49 (m, 2H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f6c09873235467fa9beb452f2bab7a9
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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