Dimethylformamide → N,N-Dimethyl-3-nitroaniline

HRID 2409436Notes

Reaction equation

HRID 2409436 reaction equation
[N+:1]([C:4]1[CH:5]=C([CH:8]=[CH:9][CH:10]=1)N)([O-:3])=[O:2].[H-].[Na+].IC.[CH3:15][N:16]([CH3:19])[CH:17]=O>>[CH3:15][N:16]([CH3:19])[C:17]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 74233-NitroanilineHCID 24758Sodium hydride

Product 1

HCID 69269N,N-Dimethyl-3-nitroanilineYield 86%

Procedure

3-nitroaniline (1.0 g, 7.25 mmol) was dissolved in N,N-dimethylformamide (50 ml), added with sodium hydride (1.7 g, 21.7 mmol) and iodomethane (2.7 ml, 21.7 mmol) at 0° C. The resulting mixture was stirred for 4 hours at room temperature and poured into ice water. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (hexane:ethyl acetate=1:1) to obtain the title compound (2.0 g, yield: 86%, yellow solid).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue was then purified by flash column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-91ace8f256754e30b8c4497fc287cc5a
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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