3-(Chloromethyl)pyridine hydrochloride → HCID 54223650, compound

HRID 1583365Notes

Reaction equation

HRID 1583365 reaction equation
[Na].[CH3:2][O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5].Cl.Cl[CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1>CO>[CH3:2][O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([O:15][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 5360545SodiumHCID 12993389HCID 12993389, compound

Product 1

HCID 54223650HCID 54223650, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (0.37 g.) was dissolved in methanol (70 ml.) and 7-hydroxybenzofuran-2-carboxylic acid methyl ester (1.54 g.) was added. The solution was stirred for 15 minutes ad then 3-chloromethylpyridine hydrochloride (1.32 g.) was added. The mixture was heated under reflux for 8 hours and then evaporated. Water was added to the residue and the mixture was extracted sevral times with ethyl acetate. The combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave a solid which was chromatographed on silica gel. Elution with chloroform gave a solid which was crystallized from methanol/water to give 7-(3-pyridylmethoxy)benzofuran-2-carboxylic acid methyl ester (1.0 g.), m.p. 117°-118° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customevaporated
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted sevral times with ethyl acetate
  6. washThe combined extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent
  9. customgave a solid which
  10. customwas chromatographed on silica gel
  11. washElution with chloroform
  12. customgave a solid which
  13. customwas crystallized from methanol/water

Sources & evidence

ORD record
ord-e27ba6171e744c8b83adccd31f7b5648
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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