Hydrochloric Acid → Picolinic acid

HRID 69966

Reaction equation

HRID 69966 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O-:9])=[O:8].[Li+].[OH-].Cl>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6920223Picolinate

Product 1

HCID 1018Picolinic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-amino-6-(2-fluoro-5-isopropylcabamoyl)phenyl)picolinate (1.0 equiv) in THF (0.5M), was added 1M LiOH (4.0 equiv). After stirring for 4 hours at 60° C., 1 N HCl (4.0 equiv.) was added and the THF was removed in vacuo. The resulting solid was filtered and rinsed with cold H2O (3×20 mL) to yield 3-amino-6-(2-fluoro-5-isopropylcabamoyl)phenyl)picolinic acid (98%). LCMS (m/z): 318.1 (MH+); LC Rt=2.4 min

Workup

  1. customthe THF was removed in vacuo
  2. filtrationThe resulting solid was filtered
  3. washrinsed with cold H2O (3×20 mL)

Sources & evidence

ORD record
ord-2bc4924df4b341d5b3a2a67aad801b75
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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