2-Pyridinemethanamine → 4-Hydroxy-6-methyl-1-pyridin-2-ylmethyl-1H-pyridin-2-one

HRID 12256

Reaktionsgleichung

Reaktionsgleichung von HRID 12256
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>O>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:4](=[O:9])[CH:3]=1

Komponenten

4

Edukt 2

HCID 195092-PyridinemethanamineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Produkt 1

HCID 547030554-Hydroxy-6-methyl-1-pyridin-2-ylmethyl-1H-pyridin-2-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 12.6 g (0.1 mol) of 4-hydroxy-6-methyl-2-pyrone in 50 ml water was added 2-(aminomethyl)pyridine (10.3 ml, 0.1 mol) and the mixture heated to reflux for 2.5 hours. The resulting light yellow compound was filtered from the cooled mixture. Concentration of the filtrate and trituration of the resulting gum with dichloromethane afforded a second crop of the title compound (19.85 g, 92%). NMR (DMSO-d6, ppm): 10.5 (s, 1H), 8.5 (d, 1H), 7.7-7.8 (t, 1H), 7.2 (t, 1H), 7.1 (d, 1H), 5.8 (s, 1H), 5.5 (s, 1H), 5.2 (s, 2H), 2.2 (s, 3H). FIA: m/z-215.1 ES−/217.1 ES+

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationThe resulting light yellow compound was filtered from the cooled mixture

Quellen und Nachweise

ORD-Eintrag
ord-81533076c8b148cfa53adb9113171694
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727992B2

Verknüpfte Notizen

Wird geladen…