Hydrochloric Acid → 3-(3-Fluorobenzyl)pyridine

HRID 1904641Notes

Reaction equation

HRID 1904641 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.Cl>[Zn].Cl[Hg]Cl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 129300293-(3-Fluorobenzoyl)pyridine

Product 1

HCID 200378593-(3-Fluorobenzyl)pyridineYield 29.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 24085Mercuric ChlorideCatalystHCID 962WaterSolvent

Procedure

Zinc amalgam prepared from zinc (41 g) and HgCl2 (4.1 g) was stirred in a mixture of 3-(3-fluorobenzoyl)pyridine (19.0 g, 0.095 mol), H2O (25 ml) and 12 N HCL (60 ml). The resulting mixture was stirred and heated at reflux for 30 hours. Occasionally during the course of the reaction HCl gas was passed through the mixture, and after 20 hours, additional zinc metal (41 g) was added. After 30 hours the reaction mixture was cooled, decanted, made strongly basic with 10% NaOH, and extracted three times with CH2Cl2. The extracts were dried (Na2SO4) and concentrated, and the residue was distilled to yield 5.2 g (29%) of 3-(3-fluorobenzyl)pyridine: bp 100°-110° C./79.99 Nm-2.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 hours
  3. temperatureAfter 30 hours the reaction mixture was cooled
  4. customdecanted
  5. extractionextracted three times with CH2Cl2
  6. dry with materialThe extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-d1362b05e0554dda92a287c95c7a7e98
Source dataset
uspto-grants-1989_06
Patent number
US04839371

Reaction notes

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