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

HRID 1626852Notes

Reaction equation

HRID 1626852 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[N+:15]([O-])=O>C1COCC1.C(O)C.[Pd]>[NH2:15][C:3]1[CH:4]=[C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:7][C:2]=1[OH:1]

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

Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate (260 mg, 1.09 mmol) in THF (6 mL) and ethanol (6 mL) was slowly added 10% Pd/C (29 mg) at room temperature. The mixture was hydrogenated for 2 hours at 43 psi and then filtered with celite pad and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=1/1.

Workup

  1. customat room temperature
  2. filtrationfiltered with celite pad
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with n-Hexane/EtOAc=1/1

Sources & evidence

ORD record
ord-f36acd3d8bf84580802d1345e8f4aeda
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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