Formaldehyde → 6-Methylnicotine, (A+-)-

HRID 1761

Reaction equation

HRID 1761 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1.[CH2:13]=O.[OH-].[Na+]>C(O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([CH3:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 127496842-Methyl-5-(pyrrolidin-2-yl)pyridine

Product 1

HCID 50207116-Methylnicotine, (A+-)-Yield 92%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

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).

Workup

  1. customInto a round bottom flask was placed
  2. temperatureThe mixture then was refluxed under nitrogen for 8 hr
  3. customThe cooled reaction mixture
  4. extractionthe solution extracted with chloroform (5×25 mL)
  5. dry with materialThe combined organic liquors were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. distillationand the resulting oil distilled under reduced pressure

Sources & evidence

ORD record
ord-acfd98fbecaf4acda872324b5f557a19
Source dataset
uspto-grants-1998_03
Patent number
US05726316

Linked notes

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