Ethyl 2-(4-nitrophenyl)propionate → Ethyl 2-(4-aminophenyl)propanoate

HRID 660333Notes

Reaction equation

HRID 660333 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH3:6])[CH3:2]>C1COCC1.CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 1

HCID 3016550Ethyl 2-(4-nitrophenyl)propionate

Product 1

HCID 118009Ethyl 2-(4-aminophenyl)propanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-Nitro-phenyl)-propionic acid ethyl ester (3.67 g) in THF (40 mL) and EtOH (40 mL) was slowly added 10% Pd/C (405 mg) at room temperature. After hydrogenated for 20 h with H2 balloon, the reaction mixture was filtered through celite pad and washed with EtOAc. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=4:1) to afford the product as pale yellow oil. (99.7%)

Workup

  1. customat room temperature
  2. filtrationthe reaction mixture was filtered through celite pad
  3. washwashed with EtOAc
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=4:1)

Sources & evidence

ORD record
ord-44bafbe5e0f84d9c9564330cb98c8fdc
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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