Nitric Acid → N-Methyl-3-nitro-5-(trifluoromethyl)pyridin-2-amine

HRID 923792Notes

Reaction equation

HRID 923792 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.S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>O>[CH3:1][NH:2][C:3]1[C:8]([N+:18]([O-:20])=[O:19])=[CH:7][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 18526206N-Methyl-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 2775319N-Methyl-3-nitro-5-(trifluoromethyl)pyridin-2-amineYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of N-methyl-(5-trifluoromethyl-pyridin-2-yl)-amine (17.3 g) and sulfuric acid (100 ml), nitric acid (12.3 g) was added drop-wise, and stirred with heating at 80° C. for 2 hours. The mixture was cooled to room temperature, and then the reaction mixture was poured into water. The precipitate was collected by filtration, washed with water, and dried under reduced pressure to give 18.8 g of N-methyl-(3-nitro-5-trifluoromethyl-pyridin-2-yl)-amine.

Workup

  1. additionwas added drop-wise
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7ec808fd21c542bfbe744b8c65ea6091
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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