Water → (2E)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-2-(cyclopropylmethoxyimino)ethanamine
Reaction equation
[Cl:1][C:2]1[C:3](/[C:12](=[N:25]/[O:26][CH2:27][CH:28]2[CH2:30][CH2:29]2)/[CH2:13][N:14]2C(=O)C3=CC=CC=C3C2=O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.O.NN.O>C(O)C>[CH:28]1([CH2:27][O:26]/[N:25]=[C:12](/[C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)\[CH2:13][NH2:14])[CH2:29][CH2:30]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To 98 mg of (E)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]phthalimide in 3 ml of ethanol, 76 mg of hydrazine monohydrate was added, and the mixture was stirred at 80° C. for 1 hour. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 5 ml of water and extracted with ethyl acetate (5 ml×3). The resulting organic layers were combined, dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using methanol-chloroform (1:10) as the eluent to obtain 65 mg of the desired product as a pale yellow oil. The oil was used in the next step without further purification.
Workup
- customAfter completion of the reaction
- temperatureto cool to room temperature
- extractionextracted with ethyl acetate (5 ml×3)
- dry with materialdried over saturated aqueous sodium chloride
- customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7c48d8780b444609839853c874645be6
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434684B2
Reaction notes
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