Hydrochloric Acid → 6-Chloro-2-(2,4-dichlorobenzoyl)-pyridine

HRID 648713Notes

Reaction equation

HRID 648713 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[N:11]=[C:10]([C:12](Cl)=[O:13])[CH:9]=[CH:8][CH:7]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1.Cl>>[Cl:5][C:6]1[N:11]=[C:10]([C:12](=[O:13])[C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][C:18]=2[Cl:22])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 109431,3-DichlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 109429766-chloropyridine-2-carbonyl Chloride

Product 1

HCID 201457146-Chloro-2-(2,4-dichlorobenzoyl)-pyridine

Procedure

40.9 g AlCl3 is added in portions to a mixture of 26.4 g 6-chloro-2-pyridinecarboxylic acid chloride and 112 g 1,3-dichlorobenzene. The mixture is slowly heated until 130°-40° C. After standing overnight, it is added to a mixture of diluted HCl and crushed ice, basified and extracted with ethyl ether. The ethereal extracts are washed with water, dried and solvent evaporated (water pump). The residual deep green oil is crystallised from ethanol:water in the presence of decolorizing carbon. Yield: 10 g title compound, m.p. 103°-4° C.; UV (ethanol): λmax. 281 nm; ε: 14,500; Cl 37.02 (37.12).

Workup

  1. temperatureThe mixture is slowly heated until 130°-40° C
  2. customcrushed ice
  3. extractionextracted with ethyl ether
  4. washThe ethereal extracts are washed with water
  5. customdried
  6. customsolvent evaporated (water pump)
  7. customThe residual deep green oil is crystallised from ethanol

Sources & evidence

ORD record
ord-cb360c11173540ef8be07646478bab67
Source dataset
uspto-grants-1988_04
Patent number
US04736037

Reaction notes

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