Phosphorus oxychloride → 6-Chloro-2,3-diphenylpyridine

HRID 1271240Notes

Reaction equation

HRID 1271240 reaction equation
[C:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:10]=[CH:9][N+:8]=2[O-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:22])=O>O>[Cl:22][C:9]1[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 229319562,3-Diphenylpyridin-1-oxide

Product 1

HCID 229320056-Chloro-2,3-diphenylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 922 mg of 2,3-diphenylpyridin-1-oxide, 3 ml of phosphorus oxychloride was added, followed by stirring at 100° C. for 15 minutes. The reaction solution was poured into iced water, extracted with ethyl acetate and then washed with an aqueous 5% potassium carbonate solution and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 428 mg of the desired compound as an oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with an aqueous 5% potassium carbonate solution and saturated brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8833518b10d94d408bd166de266f6a85
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

Loading…