Sodium cyanoborohydride → N-(2,4-dichloro-benzyl)-O-methyl-hydroxylamine
Reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12].C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[CH2:4][NH:3][O:2][CH3:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 24 °C
Procedure
A solution of 2,4-dichloro-benzaldehyde O-methyl-oxime (1.0 g, 4.9 mmol), prepared as described in example P10a, in acetic acid (7.1 ml) was treated at 10° C. with sodium cyanoborohydride (615 mg, 9.8 mmol) added in small portions over 10 minutes and the resulting solution was stirred at 24° C. for 7 hours. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with water. The aqueous phase was extracted with dichloromethane (2×20 ml), washed with brine and dried over anhydrous Na2SO4. After removal of the solvent, the residue (1510 mg) was purified by flash chromatography over silica gel (eluent: c-hexane/ethyl acetate 9:1). 690 mg (68.0% of theory) of N-(2,4-dichloro-benzyl)-O-methyl-hydroxylamine was obtained in form of a clear liquid.
Workup
- additionadded in small portions over 10 minutes
- customThe solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue
- extractionThe aqueous phase was extracted with dichloromethane (2×20 ml)
- washwashed with brine
- dry with materialdried over anhydrous Na2SO4
- customAfter removal of the solvent
- customthe residue (1510 mg) was purified by flash chromatography over silica gel (eluent: c-hexane/ethyl acetate 9:1)
Sources & evidence
- ORD record
- ord-86b2ec06d95e4ed5a1499bfaa6ed2086
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357634B2
Reaction notes
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