Benzene → Methanone, (6-chloro-3-pyridinyl)phenyl-

HRID 359252Notes

Reaction equation

HRID 359252 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:6]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=1)(=[O:7])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 27821656-Chloronicotinoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3061713Methanone, (6-chloro-3-pyridinyl)phenyl-

Procedure

To 40 ml of a solution of 5.28 g of 6-chloronicotinoyl chloride in benzene, 16 g of aluminum chloride was added under ice-cooling and the resulting mixture was heated under reflux for six hours. After cooling, the reaction mixture was poured into a solution of ice/hydrochloric acid and extracted with ether. The organic phase was washed with water and dried over anhydrous sodium sulfate. After filtering off the sodium sulfate and distilling off the solvent, 4.6 g of 3-benzoyl-6-chloropyridine was obtained. m.p.: 39°-40° C.

Workup

  1. temperaturecooling
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for six hours
  4. temperatureAfter cooling
  5. extractionextracted with ether
  6. washThe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtering off the sodium sulfate
  9. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-7a84ff9cc9ed463c94c1475d7c52eff0
Source dataset
uspto-grants-1991_03
Patent number
US05000778

Reaction notes

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