Hydrochloric Acid → Methyl 3-benzyloxypicolinate

HRID 350654Notes

Reaction equation

HRID 350654 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CC(C)=O.O>[CH2:18]([O:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

Product 1

HCID 22175081Methyl 3-benzyloxypicolinateYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Methyl 3-hydroxypicolinate (2.0 g) was dissolved in 100 ml of acetone. Potassium carbonate (3.4 g) and 3.4 ml of benzyl bromide were added to the solution, and a reaction was allowed to proceed at room temperature overnight. The reaction solution was then refluxed for 4 hr. Water (50 ml) was added thereto, and the mixture was neutralized with 1 N hydrochloric acid, followed by concentration under the reduced pressure. Methylene chloride and water were added to the residue. The organic layer was dried over magnesium sulfate, and was then dried under the reduced pressure. The dried organic layer was then purified by column chromatography (chloroform-methanol) to give 2.1 g (yield 62%) of methyl 3-benzyloxypicolinate.

Workup

  1. temperatureThe reaction solution was then refluxed for 4 hr
  2. concentrationfollowed by concentration under the reduced pressure
  3. additionMethylene chloride and water were added to the residue
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customwas then dried under the reduced pressure
  6. customThe dried organic layer was then purified by column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-e3ff4e80580e4cf8a62f5c54cab98838
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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