Dimethylformamide → 2,3-Difluoro-N-methyl-6-nitroaniline
Reaction equation
[CH3:1][N:2]([CH:4]=O)C.[F:6][C:7]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])C=1N.C(=O)([O-])[O-].[K+].[K+].CI>O>[F:6][C:7]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:4]=1[NH:2][CH3:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a DMF solution (50 mL) of 2,3-difluoro-6-nitroaniline (3.0 g) were added potassium carbonate (14.3 g), and methyl iodide (3.23 mL), and the mixture was stirred at 50° C. for 4 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.66 g).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-0fb82625773e4c068a68b47ca9c59eed
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090586B2
Reaction notes
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