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

HRID 660316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660316
[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]

Komponenten

5

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4f79ac3af27a430ba70a1775c217c213
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084484B2

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