Dimethylformamide → 4-iodo-N-methyl-2-nitroaniline

HRID 530911Notes

Reaction equation

HRID 530911 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[H-].[Na+].[CH3:14]N(C=O)C.IC>O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH3:14])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 113690724-Iodo-2-nitroaniline

Product 1

HCID 658098494-iodo-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-iodo-2-nitro-phenyl amine (2.0 g), 60% sodium hydride (oil) (330 mg), and DMF (20 ml) was added dropwise iodomethane (470 μL) while ice-cooling. The reaction mixture was heated to room temperature, and then stirred for 2 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give (4-iodo-2-nitro-phenyl)-methyl-amine (2.0 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41f4c5f6bfdb4d18a1936f4378c22929
Source dataset
uspto-grants-2016_05
Patent number
US09353110B2

Reaction notes

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