Ammonia → N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

HRID 533657Notes

Reaction equation

[CH3:1][NH:2][C:3]1[C:8](Br)=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.C(CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:27].[Cl-].[NH4+]>C(CC(=O)C)(=O)C.[Cu+2].CN1C(=O)CCC1>[CH3:1][NH:2][C:3]1[C:8]([NH2:27])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a pressure-resistant reaction container, N-methyl-(3-bromo-5-trifluoromethyl-pyridin-2-yl)-amine (0.51 g), copper (II) acetylacetone (0.11 g), acetylacetone (0.20 g), cesium carbonate (1.30 g), NMP (2 ml), and 28% of aqueous ammonia (1 ml) were added, and stirred at 120° C. for 7 hours, then at 130° C. for 3 hours. The mixture was allowed to cool to room temperature, and then saturated aqueous ammonium chloride solution was poured, 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 0.28 g of N2-methyl-5-trifluoromethylpyridin-2,3-diamin.

Workup

waitat 130° C. for 3 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-73a9e64a3bdb4b72b34675b0f3862fdb
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853238B2

Reaction notes

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