Benzoic acid, 4-hydroxy-3-nitro-, methyl ester → Methyl 3-amino-4-hydroxybenzoate

HRID 350367

Reaktionsgleichung

Reaktionsgleichung von HRID 350367
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-])=O>CO.[Pd]>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]

Komponenten

4

Edukt 1

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Produkt 1

HCID 10815Methyl 3-amino-4-hydroxybenzoateAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred mixture of methyl 4-hydroxy-3-nitrobenzoate (3.22 g, 0.0163 mol) and 5% Pd—C (12.9 g) in MeOH (30mL) was hydrogenated under an atmospheric pressure for 70 hr at room temp. Insoluble catalyst was removed, and the filtrate was evaporated in vacuo. The residue was chromatographed on silica-gel with EtOH—CHCl3 (1:20, v/v) as eluent to afford 1.89 g (69%) methyl 3-amino-4-hydroxybenzoate as a pale brown syrup.

Aufarbeitung

  1. customInsoluble catalyst was removed
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed on silica-gel with EtOH—CHCl3 (1:20, v/v) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-795f063488d54799ad89dd33cb14ff31
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

Verknüpfte Notizen

Wird geladen…