Hydrochloric Acid → Methyl 3-benzyloxy-6-methoxypicolinate

HRID 350655Notes

Reaction equation

HRID 350655 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([OH:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.CI>[CH2:1]([O:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([O:15][CH3:20])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 178499129HCID 178499129, compound

Product 1

HCID 22175139Methyl 3-benzyloxy-6-methoxypicolinateYield 49%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6328Methyl iodideSolvent

Procedure

Methyl 3-benzyloxy-6-hydroxy-picolinate (0.55 g) was dissolved in 55 ml of acetone and 20 ml of methyl iodide. Potassium carbonate (1.4 g) was added to the solution, and the mixture was refluxed for 3 hr. After cooling, the reaction solution was neutralized with 1 N hydrochloric acid, and was concentrated under the reduced pressure. Methylene chloride and water were then added to the concentrate to conduct extraction. The organic layer was dried over magnesium sulfate, and the dried organic layer was then concentrated under the reduced pressure. The residue was purified by column chromatography (chloroform-methanol) to give 0.28 g (yield 49%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. temperatureAfter cooling
  3. concentrationwas concentrated under the reduced pressure
  4. additionMethylene chloride and water were then added to the
  5. concentrationconcentrate
  6. extractionextraction
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationthe dried organic layer was then concentrated under the reduced pressure
  9. customThe residue was purified by column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-0db6c987627c41fea65370e577ffed10
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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