HCID 58201184, compound → 3-Chloro-4-methoxy-2,5-dimethylpyridine

HRID 2408894Notes

Reaction equation

HRID 2408894 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([CH2:10]Cl)[C:7]=1[O:8][CH3:9]>CO.[Pd].[C]>[Cl:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]

Participants

4

Reactant 1

HCID 58201184HCID 58201184, compound

Product 1

HCID 582012143-Chloro-4-methoxy-2,5-dimethylpyridineYield 79.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

The above 3-chloro-5-(chloromethyl)-4-methoxy-2-methylpyridine (550 mg) was dissolved in 10 ml of methanol, and 10% Pd carbon (50 mg) was then added to the solution. Normal-pressure contact hydrogenation was performed on the mixture under cooling on ice for 3 hours. Thereafter, the catalyst was removed by filtration, and methanol was then distilled away under reduced pressure. The residue was extracted with chloroform. The organic layer was washed with a saturated sodium bicarbonate solution, and it was then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by silica gel chromatography (ethyl acetate-hexane), so as to obtain the title compound (365 mg) as an oily substance.

Workup

  1. temperatureunder cooling on ice for 3 hours
  2. customThereafter, the catalyst was removed by filtration, and methanol
  3. distillationwas then distilled away under reduced pressure
  4. extractionThe residue was extracted with chloroform
  5. washThe organic layer was washed with a saturated sodium bicarbonate solution, and it
  6. dry with materialwas then dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away
  8. customthe residue was purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-de897996a8584d3a8e832f18a4a9911f
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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