Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate → Ethyl 3-amino-4-hydroxy-phenyl-propionate

HRID 1626873Notes

Reaction equation

HRID 1626873 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)[CH3:6])[CH3:2]>C1COCC1.CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([NH2:14])[CH:8]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 1

HCID 21444155Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate

Product 1

HCID 12202638Ethyl 3-amino-4-hydroxy-phenyl-propionate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-hydroxy-3-nitro-phenyl)-propionic acid ethyl ester (9.71 g) in THF (40 mL) and EtOH (40 mL) was slowly added 10% Pd/C (0.89 g) at room temperature. After being hydrogenated for 0.5 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=2:1) to afford the product as pale yellow solid.

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=2:1)

Sources & evidence

ORD record
ord-88f539a515f346c99e6c30e5e6b8ed68
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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