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

HRID 885455Notes

Reaction equation

HRID 885455 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 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 then diluted with water, and the resulting 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 then diluted with water
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with H2O and hexanes

Sources & evidence

ORD record
ord-380a6d8fad4947eca7795d184e2fa4b9
Source dataset
uspto-grants-2012_08
Patent number
US08242157B2

Reaction notes

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