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

HRID 923795Notes

Reaction equation

HRID 923795 reaction equation
BrC1C(N)=NC=C([C:8]([F:11])([F:10])[F:9])C=1.[C:13]([CH2:16][C:17](=O)[CH3:18])(=O)[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:26].[Cl-].[NH4+:28].C[N:30]1[C:34](=O)CCC1>C(CC(=O)C)(=O)C.[Cu+2]>[CH3:34][NH:30][C:18]1[C:17]([NH2:28])=[CH:16][C:13]([C:8]([F:9])([F:10])[F:11])=[CH:14][N:26]=1

Participants

8

Reactant 6

HCID 222AmmoniaHCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 25517Ammonium ChlorideHCID 31261AcetylacetoneHCID 130641553-Bromo-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 1

HCID 21863952acetylacetone copper(II)Catalyst

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

  1. waitat 130° C. for 3 hours
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5bcce03b0424176ac89c4782f17dcf1
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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