Water → 4-Methyl-6-[3-(trifluoromethyl)phenoxy] picolinic acid, (2,2,3,3,3-pentafluoropropylidene] hydrazide

HRID 1274819Notes

Reaction equation

HRID 1274819 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:5]=[C:4]([C:19]([NH:21][NH2:22])=[O:20])[CH:3]=1.O.[F:24][C:25]([F:32])([C:28]([F:31])([F:30])[F:29])[CH:26]=O.O>C(O)(=O)C.C(OCC)(=O)C.O>[F:24][C:25]([F:32])([C:28]([F:31])([F:30])[F:29])[CH:26]=[N:22][NH:21][C:19](=[O:20])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2776005HCID 2776005, compoundHCID 702663564-Methyl-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide

Product 1

HCID 867561034-Methyl-6-[3-(trifluoromethyl)phenoxy] picolinic acid, (2,2,3,3,3-pentafluoropropylidene] hydrazide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 22728543Water ethylacetateSolvent

Procedure

4-methyl-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide (0.38 g, 0.0012 mol) was dissolved in 5 ml of acetic acid. The obtained solution was mixed with 2,2,3,3,3-pentafluoropropionaldehyde monohydrate (0.40 g, 0.0012×2 mol), and then the resultant mixture was stirred at 80° C. for 3 hours. Thereafter, a chilled water was poured into the obtained reaction solution which was then distributed in ethyl acetate-water. The organic phase separated from the solution was washed with water and then dried with anhydrous sodium sulfate. After distilling off the solvent from the dried product, the obtained distillation residues were purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. customThe organic phase separated from the solution
  2. washwas washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent from the dried product
  5. distillationthe obtained distillation residues
  6. customwere purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0bf79456acdb40a98c2c28553da89a33
Source dataset
uspto-grants-2000_12
Patent number
US06159901

Reaction notes

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