Citric Acid → 3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine

HRID 235779Notes

Reaction equation

HRID 235779 reaction equation
[N:1]1[CH:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:4]=[CH:3][CH:2]=1.OO.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:18]>>[N:1]1[CH:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][N+:8]2([O-:18])[CH3:9])[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 311Citric AcidHCID 784Hydrogen PeroxideHCID 9423-(1-Methylpyrrolidin-2-yl)pyridine

Product 1

HCID 4093-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine

Conditions

Temperature
80 °C

Procedure

500 g of nicotine (3.08 mol) are slowly added dropwise to an equimolar 30% hydrogen peroxide solution containing 5.9 g of citric acid (30.8 mmol), the temperature being maintained below 90° C. After the addition has ended, the mixture is heated at 80° C. for 5 hours.

Workup

  1. temperaturethe temperature being maintained below 90° C
  2. additionAfter the addition

Sources & evidence

ORD record
ord-a8960d59cebc469091e2f3f196126c97
Source dataset
uspto-grants-1987_02
Patent number
US04641667

Reaction notes

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