Sodium Iodide → 4-Iodoaniline

HRID 1283507Notes

Reaction equation

HRID 1283507 reaction equation
[I-:1].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O>[I:1][C:7]1[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=1.[I:1][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:3]

Participants

5

Reactant 2

HCID 5238Sodium Iodide2×HCID 6115Aniline

Product 2

HCID 108934-IodoanilineHCID 119952-Iodoaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The anode compartment of the cell described in Example 19 was charged with 150 ml of water, 22.5 g of sodium iodide and 139.5 ml of aniline. The cathode compartment was charged with 300 ml of water and 45 g of sodium iodide. The cell was operated at 0.25 ampere (25 ma/cm2) at 25°C for 4 hours, and the anode solution was extracted with methylene chloride and analyzed by glc. A total of 3.30 g of p-iodoaniline and 0.14 g of o-iodoaniline were produced. This corresponds to a p-iodoaniline current efficiency of 81% and a para to ortho ratio of 95.9 to 4.1.

Workup

  1. extractionthe anode solution was extracted with methylene chloride

Sources & evidence

ORD record
ord-63bd7322908245d8ba4cc53199922f8b
Source dataset
uspto-grants-1976_08
Patent number
US03975439

Reaction notes

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