Diethyl 2-(4-nitrophenyl)malonate → 1,3-Diethyl 2-(4-aminophenyl)propanedioate

HRID 28620

Reaktionsgleichung

Reaktionsgleichung von HRID 28620
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[CH2:9]([O:8][C:6](=[O:7])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH3:10]

Komponenten

5

Edukt 2

HCID 10869708Diethyl 2-(4-nitrophenyl)malonateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 124708371,3-Diethyl 2-(4-aminophenyl)propanedioateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of crude 2-(4-nitro-phenyl)-malonic acid diethyl ester and 10% palladium on carbon in ethyl acetate (20 ml) was treated with hydrogen gas (40 psi) on a Parr shaker for 2 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate-hexane to provide 2-(4-amino-phenyl)-malonic acid diethyl ester (450 mg, 90% yield for 2 steps).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ac985974d537456bb6214e80c2d7d84c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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