Phosphorus oxychloride → 4-Chloro-2,6-dimethylpyridine

HRID 1043916Notes

Reaction equation

HRID 1043916 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[CH:5]=[C:4]([CH3:9])[N:3]=1.P(Cl)(Cl)([Cl:12])=O>>[Cl:12][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH3:9])[CH:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429033HCID 178429033, compound

Product 1

HCID 5881754-Chloro-2,6-dimethylpyridine

Conditions

Temperature
100 °C

Procedure

2,6-dimethyl-4-hydroxypyridine (1 g) was added to phosphoryl chloride (5 mL). The solution was stirred at 100° C. for six hours. The reaction mixture was partitioned by adding water, a 5 N aqueous sodium hydroxide solution and ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (1.15 g).

Workup

  1. customThe reaction mixture was partitioned
  2. additionby adding water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a8b147d4f81d4c81af3eb2ad3a5e4f69
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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