Water → 2-Chloro-3-(4-phenylbenzoyl)-pyridine

HRID 648714

Reaction equation

HRID 648714 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:17][C:18]1[N:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].O>C(=S)=S>[Cl:17][C:18]1[C:19]([C:20](=[O:21])[C:8]2[CH:9]=[CH:10][C:5]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:6][CH:7]=2)=[CH:23][CH:24]=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7095BiphenylHCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 201457202-Chloro-3-(4-phenylbenzoyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

26.7 g AlCl3 is added slowly while stirring to a solution of 9.2 g biphenyl and 10.6 g 2-chloronicotinoyl chloride in 170 ml carbon disulfide. The mixture is refluxed 5 hrs. After cooling, the S2C layer is poured off, and the residue is added to acidic ice:water, basified and extracted with methylene chloride. The combined extracts are washed, dried (MgSO4) and solvent removed in vacuo. The crude product is chromatographed on a silicagel column and eluted with benzene:ethyl acetate 15:1 Yield: 5 g of title product, m.p. 128°-32° C.; UV (ethanol): λmax. 295 nm, ε: 27,260; Cl 11.96 (12.07).

Workup

  1. temperatureThe mixture is refluxed 5 hrs
  2. temperatureAfter cooling
  3. additionthe residue is added to acidic ice
  4. extractionextracted with methylene chloride
  5. washThe combined extracts are washed
  6. dry with materialdried (MgSO4) and solvent
  7. customremoved in vacuo
  8. customThe crude product is chromatographed on a silicagel column
  9. washeluted with benzene:ethyl acetate 15:1 Yield: 5 g of title product, m.p. 128°-32° C.

Sources & evidence

ORD record
ord-97a164c852a9440abd7db4444e7420a4
Source dataset
uspto-grants-1988_04
Patent number
US04736037

Linked notes

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