Hydrochloric Acid → 3-Benzyloxy-6-methoxypicolinic acid

HRID 350656Notes

Reaction equation

HRID 350656 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:17]([O:19]C)=[O:18])=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[C:10]([C:17]([OH:19])=[O:18])=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22175139Methyl 3-benzyloxy-6-methoxypicolinate

Product 1

HCID 178176343-Benzyloxy-6-methoxypicolinic acidYield 63.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-benzyloxy-6-methoxy-picolinate (20 mg) was dissolved in 1 ml of methanol. A 1 N aqueous sodium hydroxide solution (0.33 ml) was added to the solution, and a reaction was allowed to proceed at room temperature for 3 hr. The reaction solution was then adjusted to pH 3 by the addition of 1 N hydrochloric acid. The precipitate was collected by filtration to give 12 mg (yield 63%) of the title compound.

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-62a8df38b38049d0be6ba44581fc7e36
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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