3,5-Dimethylpyridine → 4-Chloro-3,5-dimethylpyridine

HRID 2304811Notes

Reaction equation

HRID 2304811 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1>C1(C)C=CC=CC=1>[Cl:3][C:8]1[C:9]([CH3:11])=[CH:10][N:5]=[CH:6][C:7]=1[CH3:12]

Participants

4

Reactant 2

HCID 115653,5-DimethylpyridineHCID 24386Thionyl Chloride

Product 1

HCID 109971264-Chloro-3,5-dimethylpyridineYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride was loaded into a reaction vessel equipped with a stirrer, a condenser, a dropping funnel, and a nitrogen bubbler. The temperature was lowered to 0-5ℑ C. and 3,5-lutidine was added dropwise, keeping the temperature between 0 and 10ℑ C. When the addition was complete the reaction mixture was refluxed for 18 hours. The mixture was cooled to 65ℑ C. and toluene (4 volumes) were added. 1.5 volumes of the mixture were distilled under vacuum. The heavy brown precipitate was collected by filtration. The crude product was recrystallized from methanol (3 volumes). Filtration afforded the product, 4-Chloro-3,5-Lutidine, as a beige solid, this was washed with methanol and dried under vacuum at 40ℑ C.; yield: 75%.

Workup

  1. customequipped with a stirrer, a condenser, a dropping funnel
  2. additionWhen the addition
  3. temperaturewas refluxed for 18 hours
  4. temperatureThe mixture was cooled to 65ℑ C
  5. distillation1.5 volumes of the mixture were distilled under vacuum
  6. filtrationThe heavy brown precipitate was collected by filtration
  7. customThe crude product was recrystallized from methanol (3 volumes)
  8. filtrationFiltration

Sources & evidence

ORD record
ord-2797235710424c8eb8f0e53e62e59a48
Source dataset
uspto-grants-2002_08
Patent number
US06437139B1

Reaction notes

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