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

HRID 1256614
Notes
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Reaction equation

HRID 1256614 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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

Into a mixture of 17.3 g of N-methyl(5-trifluoromethylpyridin-2-yl)-amine and 100 ml of sulfuric acid was dropped 12.3 g of nitric acid, then, the mixture was stirred for 2 hours while heating at 80° C. After cooling down to room temperature, water was poured into the reaction mixture, and the deposited precipitate was filtrated, then, washed with water, then, dried under reduced pressure to obtain 18.8 g of N-methyl(3-nitro-5-trifluoromethylpyridin-2-yl)-amine.

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationthe deposited precipitate was filtrated
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-5847bb67d5674dbbbe148653720d92df
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461181B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes