Ammonia → N3-Methyl-6-(trifluoromethyl)pyridine-2,3-diamine

HRID 923810Notes

Reaction equation

HRID 923810 reaction equation
Cl[C:2]1[C:7]([NH:8][CH3:9])=[CH:6][CH:5]=[C:4]([C:10]([F:13])([F:12])[F:11])[N:3]=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>[CH3:9][NH:8][C:7]1[C:2]([NH2:27])=[N:3][C:4]([C:10]([F:13])([F:12])[F:11])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 31261AcetylacetoneHCID 14879205(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-methyl-amine

Product 1

HCID 68091240N3-Methyl-6-(trifluoromethyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 21863952acetylacetone copper(II)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To a pressure-resistant reaction container, (2-chloro-6-trifluoromethylpyridin-3-yl)-methylamine (2.60 g), copper (II) acetylacetone (0.64 g), acetylacetone (1.23 g), cesium carbonate (7.99 g), NMP (10 ml), and 28% of aqueous ammonia (7 ml) were added, and stirred at 140° C. for 8 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 N3-methyl-6-trifluoromethylpyridin-2,3-diamine.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6427db2bf0b5400d924bdc0b172a90d3
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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