Hydrochloric Acid → 3-Amino-6-(2,6-difluorophenyl)-5-fluoropicolinic acid

HRID 1499435

Reaction equation

HRID 1499435 reaction equation
[NH2:1][C:2]1[C:3]([C:17]([O:19]C)=[O:18])=[N:4][C:5]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[C:6]([F:8])[CH:7]=1.O.[OH-].[Li+].C1COCC1.Cl>O>[NH2:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[N:4][C:5]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59226608Methyl 3-amino-6-(2,6-difluorophenyl)-5-fluoropicolinate

Product 1

HCID 592265133-Amino-6-(2,6-difluorophenyl)-5-fluoropicolinic acidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 3-amino-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxylate (84.0 mg, 0.298 mmol) and lithium hydroxide, monohydrate (40.2 mg, 0.958 mmol), THF (2.0 mL) was added followed by water (1.0 mL). The mixture was heated at 50° C. for 3 h. The reaction was then cooled to 0° C. for, and 1 M HCl was added slowly until the pH reached 2. The reaction mixture was then diluted with water (20 mL), extracted with EtOAc (3×20 mL), and the combined organic extract was washed with brine (30 mL), dried over Na2SO4, and concentrated under reduced pressure to give the sub-title compound as a white solid (68.5 mg, 86%). LCMS calc. for C12H8F3N2O2 (M+H)+: m/z=269.0. found 269.0.

Workup

  1. additionwas added
  2. additionwas added slowly until the pH
  3. extractionextracted with EtOAc (3×20 mL)
  4. extractionthe combined organic extract
  5. washwas washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72612c69293f44c0a25b7c8d56717e01
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Linked notes

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