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

HRID 660292Notes

Reaction equation

HRID 660292 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-d260cc7546d1492e9c9807a0e78c78e1
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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