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

HRID 1256613Notes

Reaction equation

HRID 1256613 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 18.2 of 2-chloro-5-trifluoromethylpyridine and 100 ml of N-methylpyrrolidone was added 23.3 g of a 40% methylamine aqueous solution, and the mixture was stirred for 3 hours at room temperature. Water was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 17.3 g of N-methyl-(5-trifluoromethylpyridine-2-yl)-amine.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ddcee79c4e6940aa819529166775f089
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

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