2-Chlorobenzaldehyde → 4-[2-(2-chlorophenyl)ethyl]pyridine

HRID 1706680Notes

Reaction equation

HRID 1706680 reaction equation
ClC1C=CC=CC=1C=O.CC1C=CN=CC=1.C(OC(=O)C)(=O)C.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1>>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][CH2:32][C:33]1[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=1

Participants

5

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 7918Acetic AnhydrideHCID 79634-MethylpyridineHCID 53768664HCID 53768664, compound

Product 1

HCID 2208454-[2-(2-chlorophenyl)ethyl]pyridine

Procedure

14.1 g. (0.1 mole) of 2-chlorobenzaldehyde and 9.4 g. (0.1 mole) or 4-methylpyridine are refluxed for six hours in 40ml. of acetic anhydride. The reaction mixture is concentrated in vacuo and then dissolved in 200 ml. of chloroform. The chloroform solution is washed with aqueous sodium bicarbonate, dried with MgSO4, filtered and concentrated in vacuo. The oily residue is dissolved in isopropanol and treated with HCl in isopropanol until acidic. The crystalline hydrochloride salt is filtered, dissolved in 150 ml. of water and neutralized with aqueous sodium bicarbonate. The product is extracted with chloroform to yield 12.6 g. of oil 4-[2-(2-chlorophenyl)ethenyl]pyridine.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutiondissolved in 200 ml
  3. washThe chloroform solution is washed with aqueous sodium bicarbonate
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe oily residue is dissolved in isopropanol
  8. additiontreated with HCl in isopropanol until acidic
  9. filtrationThe crystalline hydrochloride salt is filtered
  10. dissolutiondissolved in 150 ml
  11. extractionThe product is extracted with chloroform
  12. customto yield 12.6 g

Sources & evidence

ORD record
ord-0d95838e605e4d5da6dbcc339b399268
Source dataset
uspto-grants-1980_06
Patent number
US04208415

Reaction notes

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