Hydrochloric Acid → 6-(2,6-Difluoro-4-(methylthio)phenyl)-5-fluoropicolinic acid

HRID 1499552Notes

Reaction equation

HRID 1499552 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:13][C:12]=1[F:21].[OH-].[Na+].Cl>C1COCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][C:12]=1[F:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66652477Methyl 6-(2,6-difluoro-4-(methylthio)phenyl)-5-fluoropicolinate

Product 1

HCID 706552406-(2,6-Difluoro-4-(methylthio)phenyl)-5-fluoropicolinic acidYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-[2,6-difluoro-4-(methylthio)phenyl]-5-fluoropyridine-2-carboxylate (80.0 mg, 0.255 mmol) was dissolved in THF (0.3 mL) and MeOH (0.3 mL), then 1.0 M aq. NaOH (1.28 mL, 1.28 mmol) was added. The reaction mixture was stirred at room temperature for 50 min., then neutralized with HCl (12 M) to pH=7 and concentrated under reduced pressure to remove all the solvents. The residue was dissolved in THF, dried, filtered and concentrated under vacuum to give the sub-title compound as a white powder (42 mg, 55%). LCMS calc. for C13H9F3NO2S (M+H)+: m/z=300.0. Found: 300.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove all the solvents
  3. dissolutionThe residue was dissolved in THF
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f5dd900f49b84fcfa81785ac8501190d
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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