Water → 6-(4-Fluorobenzyl)picolinic acid

HRID 927717Notes

Reaction equation

HRID 927717 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[N:12]=[C:11]([C:13]#N)[CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-:17].[Na+].[OH2:19]>>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[N:12]=[C:11]([C:13]([OH:19])=[O:17])[CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 710878706-(4-Fluorobenzyl)picolinonitrile

Product 1

HCID 710874636-(4-Fluorobenzyl)picolinic acidYield 80%

Conditions

Temperature
90 °C

Procedure

6-(4-Fluorobenzyl)picolinonitrile (24 mg, 113 μmol; CAN 1237431-32-1) and powdered sodium hydroxide (18.1 mg, 452 μmol) were dissolved in water (3 mL). The reaction mixture was heated to 90° C. for 2.5 h. Additional powdered sodium hydroxide (18.1 mg, 452 μmol) was added and heating was continued for another 2.5 h. The reaction mixture was poured onto 25 mL ice/0.1N HCl and extracted with EtOAc (2×20 mL). The combined organic layers were washed with ice water/brine (25 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (21 mg, 80%) as light yellow oil which was used in the next step without further purification. MS (EI): m/e=230.1 [M−H]−.

Workup

  1. temperatureheating
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with ice water/brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2338bd8e032f4b76a7beedc5d50036bd
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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