Sodium cyanoborohydride → HCID 58443691, compound
Reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH2:6][CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][NH:3][CH:4]([CH3:5])[CH2:6][CH2:7][C:8]1[C:9]([Cl:16])=[CH:10][C:11]([Cl:15])=[CH:12][C:13]=1[Cl:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(2,4,6-trichloro-phenyl)-butan-2-one O-methyl-oxime (0.650 g, 2.33 mmol) in acetic acid, sodiumcyanoborohydride (0.293 g, 4.66 mmol) was added. The reaction mass was stirred at room temp for 6 hours. When the TLC confirmed the completion of the reaction, the acetic acid in the reaction mass was removed by azeotropic distillation. The residue was then basified with 10% NaOH solution and it was extracted with ethyl acetate (3×30 ml). The combined ethyl acetate layers were washed with water followed by brine solution and dried over sodium sulfate before concentration. Resulting crude mass was purified by column chromatography using 60-120μ mesh silica gel and product collected at 3% ethyl acetate in hexane as eluent to give O-Methyl-N-[1-methyl-3-(2,4,6-trichloro-phenyl)-propyl]-hydroxylamine (0.6 g, 90%).
Workup
- customthe completion of the reaction
- customthe acetic acid in the reaction mass was removed by azeotropic distillation
- extractionwas extracted with ethyl acetate (3×30 ml)
- washThe combined ethyl acetate layers were washed with water
- dry with materialdried over sodium sulfate before concentration
- customResulting crude mass
- customwas purified by column chromatography
- customcollected at 3% ethyl acetate in hexane as eluent
Sources & evidence
- ORD record
- ord-112d0e5332a14e72a7681db8d1322a84
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258169B2
Reaction notes
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