Hydrochloric Acid → 4-(Pyridin-3-YL)benzoic acid hydrochloride

HRID 352722Notes

Reaction equation

HRID 352722 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)[CH:2]=1.[ClH:17]>O1CCOCC1>[ClH:17].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 4133187Methyl 4-pyridin-3-ylbenzoate

Product 1

HCID 694831834-(Pyridin-3-YL)benzoic acid hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

At room temperature, methyl 4-(3-pyridyl)benzoate (1.76 g) was dissolved in a mixed solvent of 1N hydrochloric acid (50 ml) and dioxane (50 ml), followed by heating under reflux for 4 hours. The solvent was then distilled off under reduced pressure. Tetrahydrofuran was added to the residue, followed by washing, whereby the title compound (1.55 g, 93%) was obtained as a colorless solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. distillationThe solvent was then distilled off under reduced pressure
  4. additionTetrahydrofuran was added to the residue
  5. washby washing

Sources & evidence

ORD record
ord-2eb6859311e1444da9afb28c8ff56524
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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