Methyl iodide → N-Methyl-2-nitro-4-(trifluoromethoxy)aniline

HRID 1256617Notes

Reaction equation

HRID 1256617 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[H-].[Na+].[CH3:18]I.[Cl-].[NH4+]>CN(C=O)C>[CH3:18][NH:6][C:5]1[CH:7]=[CH:8][C:9]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27757722-Nitro-4-(trifluoromethoxy)aniline

Product 1

HCID 53216875N-Methyl-2-nitro-4-(trifluoromethoxy)anilineYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2.22 g of 2-nitro-4-trifluoromethoxyaniline and 20 ml of DMF was added 0.44 g of sodium hydride (60% oily), and the mixture was stirred for 10 minutes under ice cool. To this mixture was added 1.42 g of methyl iodide, then, the mixture was stirred for 1 hour at room temperature. Into the reaction mixture, a saturated ammonium chloride aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.80 g of N-methyl-2-nitro-4-trifluoromethoxyaniline.

Workup

  1. temperaturecool
  2. stirringthe mixture was stirred for 1 hour at room temperature
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c8ad0f26c45424e934a1ca4998020e2
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

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