Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-hydroxy-5-methoxybenzoate

HRID 2102811

Reaktionsgleichung

Reaktionsgleichung von HRID 2102811
C([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([N+:21]([O-])=O)[CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].O1CCCC1>[NH2:21][C:11]1[CH:10]=[C:9]([OH:8])[C:18]([O:19][CH3:20])=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Komponenten

5

Edukt 2

HCID 22667033Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 23132473Methyl 2-amino-4-hydroxy-5-methoxybenzoateAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 1 l Schlenk flask filled with argon, methyl 4benzyloxy-5-methoxy-2-nitrobenzoate (11.60 g, 36.6 mmol) and palladium on charcoal (1.17 g, 10% Pd, 1.1 mmol Pd) were combined and tetrahydrofuran (250 mL) was added. The argon was replaced with hydrogen (1 bar), and the mixture was vigorously stirred at r.t. until completion of the reaction. The palladium was separated by filtration through a pad of celite and the solvent was removed to obtain methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol, 98%) which was used without further purification LC/ESI-MS: m/z=166 [M−CH4O+H]+; Rt=2.17 min.

Aufarbeitung

  1. customThe palladium was separated by filtration through a pad of celite
  2. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-96f0e1d9de9b48f483c376647f0bb9b6
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576090B2

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