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

HRID 660316Notes

Reaction equation

HRID 660316 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-4f79ac3af27a430ba70a1775c217c213
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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