Hydrogen iodide → 2-Iodo-5-phenylpyridine

HRID 1073927Notes

Reaction equation

HRID 1073927 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[IH:14]>>[I:14][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24841Hydrogen iodideHCID 27628682-Chloro-5-phenylpyridine

Product 1

HCID 112197482-Iodo-5-phenylpyridine

Procedure

15.98 g of 2-chloro-5-phenylpyridine were dissolved in 150 ml of 55% aqueous hydroiodic acid and the solution was heated at reflux for 2 hours. Upon cooling a solid precipitated and this was filtered off and washed with water The solid was partitioned between diethyl ether and 2M sodium hydroxide solution, and the organic phase was dried over sodium sulphate and evaporated to give 15.87 g of 2-iodo-5-phenylpyridine which was used without further purification.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 hours
  3. temperatureUpon cooling a solid
  4. customprecipitated
  5. filtrationthis was filtered off
  6. washwashed with water The solid
  7. customwas partitioned between diethyl ether and 2M sodium hydroxide solution
  8. dry with materialthe organic phase was dried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-d74ee7c47a314cf4983ce1eea287b83c
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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