Benzene → 2,6-Dibenzoylpyridine

HRID 1841513Notes

Reaction equation

HRID 1841513 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].Cl[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](Cl)=[O:15])[N:9]=1)=[O:7].O.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:15])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]=1)(=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 773352,6-Pyridinedicarbonyl dichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3166562,6-DibenzoylpyridineYield 58%

Conditions

Temperature
60 °C

Procedure

Aluminium trichloride (5.1 g, 3.18 mmol) was added to a suspension of 2,6-bis(chlorocarbonyl)pyridine (3.7 g, 18 mmol) in 200 ml of benzene. The reaction mixture was heated to 60° C. and kept at that temperature for 4 h and subsequently for 16 h at room temperature. The mixture was poured into water, the organic layer was separated and evaporated to dryness. The residue was dissolved in CH2Cl2 and filtered. Removal of CH2Cl2 in vacuum yielded 3.0 g (58%) of product.

Workup

  1. customthe organic layer was separated
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. filtrationfiltered
  5. customRemoval of CH2Cl2 in vacuum

Sources & evidence

ORD record
ord-48fbbee0fd4c4da082c56e3bc44acdc8
Source dataset
uspto-grants-2004_01
Patent number
US06683187B2

Reaction notes

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