Reaction #1857

Reaction equation

XVI

6-Methylnomicotine

formaldehyde

sodium hydroxide

→

XVII

Yield 92.0%

(+/-)-6-Methylnicotine

Yield 92.0%

Solvents

formic acid

Conditions

Workup

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

Procedure

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).

Source