Methylamine → N-Methyl-5-(trifluoromethyl)pyridin-2-amine

HRID 533653Notes

Reaction equation

HRID 533653 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH3:12][N:13]1CCCC1=O.CN>O>[CH3:12][NH:13][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 18526206N-Methyl-5-(trifluoromethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-chloro-5-trifluoromethylpyridine (18.2) and N-methylpyrrolidone (100 ml), 40% of aqueous methylamine solution (23.3 g) was added, and stirred at room temperature for 3 hours. Water was poured thereinto, and extracted with ethyl acetate 3 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 17.3 g of N-methyl-(5-trifluoromethyl-pyridin-2-yl)-amine.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate 3 times
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-495140a5e3fd4262a063ca4e7191c7a3
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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