Tetrahydrofuran → Ethyl 5-aminonaphthalene-1-carboxylate

HRID 1610191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610191
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-])=O.O1CCCC1>C(O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 285289Ethyl 5-nitro-1-naphthoate

Produkt 1

HCID 22261675Ethyl 5-aminonaphthalene-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 5-nitro-1-naphthoate (3.304 g, 13.47 mmol) in ethanol (10 ml)-tetrahydrofuran (20 ml) was hydrogenated under normal temperature and normal pressure using 10% palladium/carbon (containing water by 50%) (0.5 g) as a catalyst until the starting material disappeared. The catalyst was filtered off and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained crude product
  4. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  5. customto give the objective substance

Quellen und Nachweise

ORD-Eintrag
ord-721e4abc6c6846f6afcdb788475bc835
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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