2-Hydroxy-4-nitro-benzoic acid tetrahydro-pyran-4-yl ester → 4-Amino-2-hydroxy-benzoic acid tetrahydro-pyran-4-yl ester

HRID 1910823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910823
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[OH:18])[CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[OH:18])[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 671063992-Hydroxy-4-nitro-benzoic acid tetrahydro-pyran-4-yl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 612883814-Amino-2-hydroxy-benzoic acid tetrahydro-pyran-4-yl esterAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Hydroxy-4-nitro-benzoic acid tetrahydro-pyran-4-yl ester (0.32 g, 1.20 mmol) was hydrogenated in ethanol (25 mL) with 10% palladium on charcoal catalyst (70 mg) until hydrogen uptake ceased. The mixture was filtered through Celite and concentrated to give a residue which was purified by flash column chromatography on silica, eluting with ethyl acetate/petroleum ether (5-35% gradient) to give 4-amino-2-hydroxy-benzoic acid tetrahydro-pyran-4-yl ester (100 mg, 35%).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto give a residue which
  4. customwas purified by flash column chromatography on silica
  5. washeluting with ethyl acetate/petroleum ether (5-35% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-507420eddd44400785df3ac27af18704
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604029B2

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