Reaktion #1857

Reaktionsgleichung

XVI

6-Methylnomicotine

formaldehyde

sodium hydroxide

→

XVII

Ausbeute 92.0%

(+/-)-6-Methylnicotine

Ausbeute 92.0%

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a round bottom flask was placed
2. 2
   TemperaturThe mixture then was refluxed under nitrogen for 8 hr
3. 3
   SonstigeThe cooled reaction mixture
4. 4
   Extraktionthe solution extracted with chloroform (5×25 mL)
5. 5
   TrocknenThe combined organic liquors were dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   workup.DISTILLATIONand the resulting oil distilled under reduced pressure

Vorschrift

Into a round bottom flask was placed XVI (2.0 g), and formaldehyde (37% w/v in water, 20 mL) and formic acid (95-97% w/v, 45 mL), both a 0° C., were added. The mixture then was refluxed under nitrogen for 8 hr. The cooled reaction mixture was basified with aqueous sodium hydroxide (50% w/v) to pH 8-9, and the solution extracted with chloroform (5×25 mL). The combined organic liquors were dried over anhydrous sodium sulfate, filtered and evaporated; and the resulting oil distilled under reduced pressure to afford XVII as a clear odorless oil (b.p. 107° C. at 3 mm Hg, 92% yield).

Quelle