O-ethylhydroxylamine hydrochloride → 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-ethyloxime
Reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][N:6]=1)=O.Cl.[CH2:14]([O:16][NH2:17])[CH3:15]>C(O)C>[CH2:14]([O:16][N:17]=[C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][N:6]=1)[CH2:2][Br:1])[CH3:15]Participants
Procedure
To 3.00 g of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone in 25 ml of ethanol, 1.09 g of ethoxyamine hydrochloride was added, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, the resulting residue was mixed with 50 ml of water and extracted with ethyl acetate (50 ml×2), the resulting organic layers were combined, washed with water (50 ml×1) and 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 chromatograph using ethyl acetate-hexane (with a gradient of from 5:95 to 15:85) as the eluent to obtain 3.03 g of the desired product as a colorless oil.
Workup
- customAfter completion of the reaction
- customthe solvent was evaporated under reduced pressure
- additionthe resulting residue was mixed with 50 ml of water
- extractionextracted with ethyl acetate (50 ml×2)
- washwashed with water (50 ml×1)
- 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 chromatograph
Sources & evidence
- ORD record
- ord-d7886ecb0d194d838c88aa037cc40847
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434684B2
Reaction notes
Loading…