Hydrochloric Acid → 3-Benzoyl-2-chloropyridine

HRID 65530

Reaction equation

HRID 65530 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[Cl:9][C:10]1[C:15]([C:16]#N)=[CH:14][CH:13]=[CH:12][N:11]=1.Cl.CC[O:21]CC>>[C:16]([C:15]1[C:10]([Cl:9])=[N:11][CH:12]=[CH:13][CH:14]=1)(=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 7961BromobenzeneHCID 810792-ChloronicotinonitrileHCID 5462224Magnesium

Product 1

HCID 8246193-Benzoyl-2-chloropyridine

Procedure

A solution of 3.14 g (0.02 mols) bromobenzene in anhydrous ether is added dropwise to a suspension of 0.02 mols magnesium in anhydrous ether. The mixture is refluxed 1.5 hr. and is then cooled until room temperature. Now a solution of 1.38 g 2-chloro-3-cyanopyridine in 25 ml anhydrous ether is added slowly while stirring. The reaction mixture is refluxed 24 hrs. and there is added, after standing, 10% aqueous HCl. The aqueous layer is separated and the ethereal layer is washed with 25% aqueous HCl. The combined washings and the first aqueous layer are basified with 40% NaOH and extracted with ether. The combined extracts are dried (MgSO4) and solvent evaporated. The crude is distilled in vacuo. Yield: 0.8 g of title product, identical with that described in Ex. 1b.

Workup

  1. temperatureThe mixture is refluxed 1.5 hr
  2. temperatureThe reaction mixture is refluxed 24 hrs
  3. additionand there is added
  4. customThe aqueous layer is separated
  5. washthe ethereal layer is washed with 25% aqueous HCl
  6. extractionextracted with ether
  7. dry with materialThe combined extracts are dried (MgSO4) and solvent
  8. customevaporated
  9. distillationThe crude is distilled in vacuo

Sources & evidence

ORD record
ord-da0ee5390b2f4460ba4acde2f5dfb0a5
Source dataset
uspto-grants-1986_09
Patent number
US04614833

Linked notes

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