Potassium Iodide → 4-Iodo-2-nitroaniline

HRID 1673069Notes

Reaction equation

HRID 1673069 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[I-].[K+].[I:13]([O-])(=O)(=O)=O.[K+].[Cl-].[Na+]>C(O)(=O)C.O>[I:13][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 69462-Nitroaniline2×HCID 516896Potassium periodate

Product 1

HCID 113690724-Iodo-2-nitroanilineYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a round bottom flask, a mixture of o-nitro aniline (formula 4) (13.7 g, 100 mmol), and potassium iodide (16.6 g, 100 mmol), potassium periodate (21.4 g, 100 mmol), sodium chloride (11.7 g, 200 mmol) in acetic acid and water (9:1) was stirred for 8-15 hours at room temperature. The reaction mixture was then poured over chopped ice and extracted with dichloromethane. The extract was further washed twice with water, then brine solution and dried over anhydrous sodium sulfate. On removal of dichloromethane 4-iodo-2-nitro aniline (formula 3) was obtained in 100% yield (26.4 g). The product was analyzed by the analytical methods like 1H & 13C NMR and GC-MS for its purity.

Workup

  1. additionThe reaction mixture was then poured over chopped ice
  2. extractionextracted with dichloromethane
  3. washThe extract was further washed twice with water
  4. dry with materialbrine solution and dried over anhydrous sodium sulfate
  5. customOn removal of dichloromethane 4-iodo-2-nitro aniline (formula 3)
  6. customwas obtained in 100% yield (26.4 g)

Sources & evidence

ORD record
ord-c32bff3ac5d74a3b83a24dd95a10cbe2
Source dataset
uspto-grants-2011_08
Patent number
US07999112B2

Reaction notes

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