Potassium Iodide → 1-(4-chlorobutyl)-4-methylpyridin-2(1H)-one

HRID 2194379Notes

Reaction equation

HRID 2194379 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][CH2:18][CH2:19][Cl:20].[I-].[K+]>CO.O>[Cl:20][CH2:19][CH2:18][CH2:17][CH2:16][N:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]1=[O:1]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178428601HCID 178428601, compound

Product 1

HCID 592346451-(4-chlorobutyl)-4-methylpyridin-2(1H)-oneYield 72.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-hydroxy-4-methylpyridine (1.50 g, 13.75 mmol) and potassium carbonate (1.90 g, 13.75 mmol) in 13 ml of methanol were stirred at room temperature for 15 minutes and then 1-bromo-4-chlorobutane (3.54 g, 20.62 mmol) and a spatula tip of potassium iodide were added thereto. The reaction mixture was heated to reflux for 6 hours and then stirred at room temperature for 12 hours. Water was then added to the reaction mixture, and the aqueous mixture was extracted with dichloromethane. Drying of the organic phase and removal of the desiccant by filtration was followed by concentration of the organic phase in vacuo. Flash chromatography of resulting residue on silica gel (eluent: CH2Cl2/CH3OH: 98:2) afforded 2.0 g of 1-(4-chlorobutyl)-4-methylpyridin-2(1H)-one.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 hours
  3. stirringstirred at room temperature for 12 hours
  4. extractionthe aqueous mixture was extracted with dichloromethane
  5. customDrying of the organic phase and removal of the
  6. filtrationdesiccant by filtration

Sources & evidence

ORD record
ord-2890c12eea07458a84cc18524000dd1f
Source dataset
uspto-grants-2012_12
Patent number
US08334289B2

Reaction notes

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