2-Methyl-3-nitroaniline → 4-Iodo-2-methyl-3-nitrobenzenamine

HRID 1985452Notes

Reaction equation

HRID 1985452 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])O.[Na+].[I:17]Cl>CO>[I:17][C:7]1[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([CH3:1])[C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 117832-Methyl-3-nitroanilineHCID 24640Iodine chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 597319804-Iodo-2-methyl-3-nitrobenzenamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a well stirred solution of 2-methyl-3-nitroaniline (10 g, 66 mmol) in methanol (150 mL) was added sodium hydrogencarbonate (264 mmol) followed by 1.0 M solution of iodine monochloride (72 mmol) at room temperature. After stirring for 1 h, the solvent was removed, diluted with ether, washed with 10% aqueous sodium thiosulfate solution. The solvent was removed and the crude iodide was in the next step.

Workup

  1. customthe solvent was removed
  2. additiondiluted with ether
  3. washwashed with 10% aqueous sodium thiosulfate solution
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-9d8b05e15a7743bca3355e59000ec307
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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