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

HRID 2165502Notes

Reaction equation

HRID 2165502 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-724ea84bebd94d9490893e8f35188ede
Source dataset
uspto-grants-1990_07
Patent number
US04940483

Reaction notes

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