Benzene → 3-Benzoyl-2-chloropyridine

HRID 648709Notes

Reaction equation

HRID 648709 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].O.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:4]([C:3]1[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8246193-Benzoyl-2-chloropyridine

Procedure

To a cooled solution of 150 g 2-chloro-nicotinoyl chloride in 400 ml benzene there is added slowly 238 g AlCl3. After refluxing 2 hrs. the reaction mixture is added with stirring to a slightly acidic ice: water mixture. The organic layer is separated and the aqueous one is extracted with ethyl ether. The combined organic layers are washed with HONa 1N, then with water, and dried over Na2SO4. The excess benzene is distilled at water pump pressure in a rotary evaporator and the residual oil is distilled in vacuo. Yield: 157 g of title product, b.p. 123° C./0.05 mm; m.p. 35°-7° C.; UV (ethanol): λmax. 254 nm., ε: 17,180; Cl 15.97 (16.29).

Workup

  1. temperatureAfter refluxing 2 hrs
  2. additionthe reaction mixture is added
  3. customThe organic layer is separated
  4. extractionthe aqueous one is extracted with ethyl ether
  5. washThe combined organic layers are washed with HONa 1N
  6. dry with materialwith water, and dried over Na2SO4
  7. distillationThe excess benzene is distilled at water pump pressure in a rotary evaporator
  8. distillationthe residual oil is distilled in vacuo

Sources & evidence

ORD record
ord-ef3affb0918342708ced581bb98ca27d
Source dataset
uspto-grants-1988_04
Patent number
US04736037

Reaction notes

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