HCID 86242284, compound → HCID 12159859, compound

HRID 1404873Notes

Reaction equation

HRID 1404873 reaction equation
[C:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N+:12]([O-])=O)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[CH:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH2:12])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 86242284HCID 86242284, compound

Product 1

HCID 12159859HCID 12159859, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(cyclopent-1-en-1-yl)-2-nitrobenzene (0.58 g, 3.0 mmol) in ethyl acetate (30 mL) in a 200 mL roundbottom flask equipped with a magnetic stir bar and nitrogen inlet was added palladium on carbon (0.63 g, 0.30 mmol, 5%). The flask was evacuated and purged with nitrogen (3×), and then evacuated and placed under hydrogen (1 atmosphere (atm)). The mixture was stirred at room temperature overnight, filtered through a pad of Celite®, and the filter cake washed with ethyl acetate. The filtrate was concentrated to provide the title compound (0.46 g, 2.9 mmol, 98% yield) as a clear and slightly red oil: 1H NMR (400 MHz, CDCl3) δ 7.14 (dd, J=7.7, 1.3 Hz, 1H), 7.02 (td, J=7.6, 1.5 Hz, 1H), 6.76 (td, J=7.4, 1.1 Hz, 1H), 6.68 (dd, J=7.8, 1.2 Hz, 1H), 3.66 (bs, 2H), 3.04-2.92 (m, 1H), 2.13-1.98 (m, 2H), 1.88-1.58 (m, 6H); 13C NMR (101 MHz, CDCl3) δ 144.12, 130.34, 126.51, 125.95, 118.78, 115.70, 39.89, 32.17, 25.21; ESIMS m/z 162 ([M+H]+).

Workup

  1. customThe flask was evacuated
  2. custompurged with nitrogen (3×)
  3. customevacuated
  4. filtrationfiltered through a pad of Celite®
  5. washthe filter cake washed with ethyl acetate
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-608acd10f79a454581044b9aa301e74f
Source dataset
uspto-grants-2014_12
Patent number
US08916183B2

Reaction notes

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