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

HRID 533656Notes

Reaction equation

HRID 533656 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-0b20f37117f74f14a87396a3dca8419c
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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