Methyl iodide → N,5-Dimethyl-2-nitroaniline

HRID 875183Notes

Reaction equation

HRID 875183 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[H-].[Na+].I[CH3:15]>CN(C=O)C>[CH3:15][NH:8][C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 113566-Nitro-m-toluidineHCID 24758Sodium hydride

Product 1

HCID 10103510N,5-Dimethyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-methyl-2-nitro-phenylamine (3.04 g, 20.0 mmol) in anhydrous DMF (20 mL) at 0° C. was portionwise added 95% NaH (528 mg, 22.0 mmol) and the resulting mixture stirred for 10 min. A solution of iodomethane (1.25 mL, 20.0 mmol) in anhydrous DMF (10 mL) was then added. The ice bath was removed and the resulting mixture was stirred at room temperature overnight. The resulting mixture was diluted with water, the solid was collected by filtration, washed with H2O and hexanes to yield methyl-(5-methyl-2-nitro-phenyl)-amine MS 167 (M+1)+.

Workup

  1. customat 0° C.
  2. customThe ice bath was removed
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. additionThe resulting mixture was diluted with water
  5. filtrationthe solid was collected by filtration
  6. washwashed with H2O and hexanes

Sources & evidence

ORD record
ord-0ad58647a4ca444ebe49bf7da12314ee
Source dataset
uspto-grants-2015_03
Patent number
US08981113B2

Reaction notes

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