Water → 6-(3-(Trifluoromethyl)phenoxy)picolinic acid

HRID 1274835Notes

Reaction equation

HRID 1274835 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=1)#N.[OH2:20].C(OCC)(=O)C.[OH2:27]>Cl>[F:17][C:16]([F:19])([F:18])[C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][C:5]1[N:4]=[C:3]([C:1]([OH:27])=[O:20])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12009738HCID 12009738, compoundHCID 22728543Water ethylacetate

Product 1

HCID 42717756-(3-(Trifluoromethyl)phenoxy)picolinic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-cyano-6-[3-(trifluoromethyl)phenoxy] pyridine (3.00 g, 0.011 mol) was suspended in about 15 ml of concentrated hydrochloric acid. The obtained suspension was stirred at about 100° C. for about 2 hours. After being allowed to stand for cooling, the obtained reaction solution was mixed with water, and then distributed in ethyl acetate-water. The organic phase separated from the solution was washed with saturated brine, dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. temperaturefor cooling
  2. customthe obtained reaction solution
  3. customThe organic phase separated from the solution
  4. washwas washed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7ba1d91ecb9749d4af7bc77b93453abd
Source dataset
uspto-grants-2000_12
Patent number
US06159901

Reaction notes

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