Hydrochloric Acid → 3-Amino-6-(thiazol-2-yl)picolinic acid

HRID 69965Notes

Reaction equation

HRID 69965 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([O:15]C)=[O:14])=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1>[NH2:1][C:2]1[C:3]([C:13]([OH:15])=[O:14])=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66652946Methyl 3-amino-6-(thiazol-2-yl)picolinate

Product 1

HCID 666524203-Amino-6-(thiazol-2-yl)picolinic acidYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-amino-6-(thiazol-2-yl)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-(thiazol-2-yl)picolinic acid (61%). LCMS (m/z): 222.1 (MH+); LC Rt=1.9 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-cabe14542fdf49d7970810eb450b1b61
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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