3-(Chloromethyl)pyridine hydrochloride → HCID 13388141, compound

HRID 638012Notes

Reaction equation

HRID 638012 reaction equation
[CH3:1][C:2]1[CH:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.Cl.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1.[O:20]1CCOCC1>>[CH3:1][C:2]1[C:10]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 312751,4-DioxaneHCID 15620341HCID 15620341, compound

Product 1

HCID 13388141HCID 13388141, compound

Procedure

To a solution of 110 g of 2-methylpyrazolo[1,5-a]pyridine in 600 ml of 1,4-dioxane was added 150 g of nicotinyl chloride hydrochloride with stirring. The resulting solution was heated to reflux for 2 hours, and after removal of solvent in vacuo, the residue was dissolved in 500 ml of water and neutralized with potassium carbonate. The aqueous layer was extracted with 500 ml of benzene, the extract was dried over anhydrous Na2SO4, and after removal of solvent, the residue was recrystallized from ethyl acetate-hexane to afford 110 g of the title compound. Concentrating the mother liquors gave a second crop of crystals, which weighed 10 g; total yield 120 g (61%), mp 89°-90° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 2 hours
  3. customafter removal of solvent in vacuo
  4. dissolutionthe residue was dissolved in 500 ml of water and neutralized with potassium carbonate
  5. extractionThe aqueous layer was extracted with 500 ml of benzene
  6. dry with materialthe extract was dried over anhydrous Na2SO4
  7. customafter removal of solvent
  8. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1081ff42030a4dfaa106bda6327f8d16
Source dataset
uspto-grants-1985_12
Patent number
US04559402

Reaction notes

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