Phosphorus oxychloride → 2-Chloro-5-(4-chlorophenyl)pyridine

HRID 1733572Notes

Reaction equation

HRID 1733572 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=O)[NH:12][CH:13]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:13][N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 102623725-(4-Chlorophenyl)-2-hydroxypyridine

Product 1

HCID 100365542-Chloro-5-(4-chlorophenyl)pyridine

Procedure

A mixture of 22.27 g. of 5-(4-chlorophenyl)-2(1H)-pyridinone and 100 ml. of phosphorus oxychloride is refluxed for 16 hours, chilled and poured onto cracked ice. The solid formed is collected by filtration and then is dissolved in chloroform. The chloroform solution is washed with water and with saturated sodium bicarbonate and then is dried over magnesium sulfate. The solvent is evaporated at reduced pressure to yield 21.1 g. of the product of the Example as a gray solid, m.p. 113°-115° C.

Workup

  1. additionA mixture of 22.27 g
  2. temperaturechilled
  3. additionpoured
  4. customThe solid formed
  5. filtrationis collected by filtration
  6. dissolutionis dissolved in chloroform
  7. washThe chloroform solution is washed with water and with saturated sodium bicarbonate
  8. dry with materialis dried over magnesium sulfate
  9. customThe solvent is evaporated at reduced pressure
  10. customto yield 21.1 g

Sources & evidence

ORD record
ord-664a29ce737d4a28899c2c1be96663e1
Source dataset
uspto-grants-1980_12
Patent number
US04242515

Reaction notes

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