Ammonium Chloride → 3-bromo-N-methyl-5-(trifluoromethyl)pyridin-2-amine

HRID 923794Notes

Reaction equation

HRID 923794 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1.[Br:13]N1C(=O)CCC1=O.[Cl-].[NH4+]>CN(C=O)C>[CH3:1][NH:2][C:3]1[C:8]([Br:13])=[CH:7][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67184N-bromobutanimideHCID 18526206N-Methyl-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 679813233-bromo-N-methyl-5-(trifluoromethyl)pyridin-2-amineYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-methyl-(5-trifluoromethyl-pyridin-2-yl)-amine (3.48 g) and DMF (20 ml), N-bromosuccinimide (4.27 g) was added, and stirred at room temperature for 1 hour. Into the reaction mixture, 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 4.8 g of N-methyl-(3-bromo-5-trifluoromethyl-pyridin-2-yl)-amine.

Workup

  1. additionwas added
  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-ae2d8eac312e462f8f7915a32a8e413d
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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