Sodium Hydroxide → 4-Amino-1-naphthaldehyde

HRID 1166788

Reaktionsgleichung

Reaktionsgleichung von HRID 1166788
[S].[N+:2]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH3:15])=[CH:7][CH:6]=1)([O-])=O.[OH-:16].[Na+]>C(O)C.C(OCC)(=O)C>[NH2:2][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[O:16])=[CH:7][CH:6]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 701554-Methyl-1-nitronaphthaleneHCID 5362487Sulfur

Produkt 1

HCID 229991604-Amino-1-naphthaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirring boiling solution of sulfur (3.7 g) in 12% aqueous NaOH (50 mL) was added a solution of 4-nitro-1-methylnaphthalene (8 g) in ethanol (50 mL). After refluxing the solution for one hour, the reaction was diluted with 500 mL of ethyl acetate and washed with water and brine, dried over MgSO4, and concentrated. The product was purified via silica gel column chromatography using ethyl acetate:hexane (5:95 to 10:90). The product (2.54 g, 34%) was stored at −78° C.

Aufarbeitung

  1. temperatureAfter refluxing the solution for one hour
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified via silica gel column chromatography
  6. customwas stored at −78° C.

Quellen und Nachweise

ORD-Eintrag
ord-8d668a3fd8f045c186ceef8d2ef27b55
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613942B1

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