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

HRID 1499556Notes

Reaction equation

HRID 1499556 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[N:17]=[C:16]([C:18]([O:20]C)=[O:19])[CH:15]=[CH:14][C:13]=1[F:22].[OH-].[Na+].Cl>C1COCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[C:12]1[N:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[CH:14][C:13]=1[F:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70655092Methyl 6-(2,6-difluoro-4-(methylsulfinyl)phenyl)-5-fluoropicolinate

Product 1

HCID 706546086-(2,6-Difluoro-4-(methylsulfinyl)phenyl)-5-fluoropicolinic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridine-2-carboxylate (37.0 mg, 0.112 mmol) was dissolved in THF (0.12 mL) and MeOH (0.12 mL), and 1.0 M aq. NaOH (0.56 mL, 0.56 mmol) was then added. The reaction mixture was stirred at room temperature for 50 min. The mixture was 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 reduced pressure to give the sub-title compound as a white powder. LCMS calc. for C13H9F3NO3S (M+H)+: m/z=316.0. Found: 316.2.

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 reduced pressure

Sources & evidence

ORD record
ord-a3bb71bb20c047a497f33cc37ee29cdd
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

Loading…