2-(Methylamino)ethanol → 1-{6-[(2-Hydroxyethyl)(methyl)amino]naphthalen-2-yl}ethan-1-one

HRID 650452

Reaktionsgleichung

Reaktionsgleichung von HRID 650452
OS([O-])=O.[Na+].O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17](=[O:19])[CH3:18])[CH:11]=[CH:10]2.[CH3:20][NH:21][CH2:22][CH2:23][OH:24]>O.C(OCC)(=O)C>[OH:24][CH2:23][CH2:22][N:21]([CH3:20])[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17](=[O:19])[CH3:18])[CH:11]=[CH:10]2

Komponenten

6

Edukt 3

HCID 80162-(Methylamino)ethanolHCID 826311-(6-Hydroxy-2-naphthyl)ethan-1-oneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 187611211-{6-[(2-Hydroxyethyl)(methyl)amino]naphthalen-2-yl}ethan-1-oneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4.15 g (55.5 mmol) NaHSO3, 8 mL of water, 0.78 g (4.19 mmol) of 1-(6-hydroxy-2-naphthyl)-1-ethanone (prepared as described in Example 1(b)), and 8 mL of 2-methylaminoethanol was heated and stirred in a steel bomb at 140° C. for 28 hours. After cooling, the mixture was distributed between ethyl acetate and water (500 mL and 200 mL, respectively). The organic layer was dried and evaporated to leave raw 1-(6-(2-hydroxyethyl-methylamino)-2-naphthyl)-1-ethanone (0.749 g, 73%) of which was further purified by radial chromatography (4 mm SiO3, CH2Cl2).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. customThe organic layer was dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3f12de9b3cec48ca8929e082b8c70a1c
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274119B1

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