Methylamine → N2-Methyl-6-(trifluoromethyl)pyridine-2,3-diamine
Reaction equation
N[C:2]1[C:3](Cl)=[N:4]C=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:13](CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:26][NH2:27].[Cl-].[NH4+:29]>C(CC(=O)C)(=O)C.[Cu+2].CN1C(=O)CCC1>[CH3:26][NH:27][C:13]1[C:3]([NH2:4])=[CH:2][CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[N:29]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a pressure-resistant reaction container, 3-amino-2-chloro-5-trifluoromethylpyridine (5 g), copper (II) acetylacetone (1.31 g), acetylacetone (2.50 g), cesium carbonate (16.25 g), NMP (20 ml), and 40% of aqueous methylamine solution (15 ml) were added, and stirred at 100° C. for 3 hours, at 120° C. for 3 hours, then at 140° C. for 5 hours. After the mixture was allowed to cool to room temperature, saturated aqueous ammonium chloride solution was poured thereinto, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.09 g of N2-methyl-6-trifluoromethylpyridin-2,3-diamine.
Workup
- waitat 140° C. for 5 hours
- temperatureto cool to room temperature
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2f8ead4ed3804000850e2afbf1c62428
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278983B2
Reaction notes
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