Hydrazine hydrate (1:1) → 4-Methyl-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]=1.O.[NH2:24][NH2:25]>CO>[CH3:10][C:8]1[CH:7]=[C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]=[C:4]([C:3]([NH:24][NH2:25])=[O:2])[CH:9]=1Participants
4
Procedure
4-methyl-6-[3-(trifluoromethyl)phenoxy] picolinic acid methyl ester (0.507 g, 0.00163 mol) was dissolved in 10 ml of methanol, and then mixed with hydrazine monohydrate (0.816 g, 0.00163×10 mol). The resultant mixture was refluxed for about 3 hours. The obtained reaction solution was concentrated, and the obtained residues were distributed in ethyl acetate-saturated sodium bicarbonate water. The organic phase separated from the solution was washed with water and then dried with anhydrous sodium sulfate. After distilling off the solvent, the obtained residues were purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.
Workup
- customThe obtained reaction solution
- concentrationwas concentrated
- customThe organic phase separated from the solution
- washwas washed with water
- dry with materialdried with anhydrous sodium sulfate
- distillationAfter distilling off the solvent
- customthe obtained residues were purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-473f162ccfae4d5492918a1ecf5c2bdf
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06159901
Reaction notes
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