Sodium Hydroxide → HCID 59226388, compound

HRID 2046884Notes

Reaction equation

HRID 2046884 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[N:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[N:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59226612HCID 59226612, compound

Product 1

HCID 59226388HCID 59226388, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 6-(2,6-difluoro-3-methylphenyl)picolinate (1.0 equiv.) in THF was added sodium hydroxide (10 equiv.) and the reaction was stirred for 2 hours. The solution was diluted with ethyl acetate and washed with 1N NaOH (2×). The combined basic aqueous washes were combined and acidified with concentrated HCl. The acidic aqueous phase was extracted with ethyl acetate (2×), the combined organic layers were dried with magnesium sulfate, filtered, and concentrated in vacuo to provide 6-(2,6-difluoro-3-methylphenyl)picolinic acid as a white solid in 85% yield. LC/MS=250.0 (M+H), Rt=0.76 min.

Workup

  1. washwashed with 1N NaOH (2×)
  2. extractionThe acidic aqueous phase was extracted with ethyl acetate (2×)
  3. dry with materialthe combined organic layers were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c654b1e14ffe41ac9dd61bd7dac53ee1
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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