3,5-diiodonitrobenzene → 3,5-DIIODOANILINE

HRID 486835Notes

Reaction equation

HRID 486835 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[C:6]([I:8])[CH:7]=1>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([I:8])[CH:7]=1)[NH2:9]

Participants

3

Reactant 1

HCID 121342563,5-diiodonitrobenzene

Product 1

HCID 121342543,5-DIIODOANILINEYield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 61.5 g (0.164M) of 3,5-diiodonitrobenzene and 111.1 g (0.4924M) of stannous chloride in 900 mL of ethanol was heated to reflux 1.5 hrs under nitrogen. The reaction mixture was cooled and most of the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and excess ice-cold 5N sodium hydroxide and ice. The organic phase was separated, washed with sat'd sodium chloride solution, and dried over anhyd. magnesium sulfate. Solvent removal afforded a crude oil which was purified on silica gel using 8:1:1 mixture of hexane:methylene chloride:ethyl acetate to give 35 g of 3,5-diiodoaniline as a light tan colored solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux 1.5 hrs under nitrogen
  3. temperatureThe reaction mixture was cooled and most of the solvent
  4. customwas removed in vacuo
  5. customThe residue was partitioned between ethyl acetate and excess ice-cold 5N sodium hydroxide and ice
  6. customThe organic phase was separated
  7. washwashed with sat'd sodium chloride solution
  8. customdried over anhyd
  9. customSolvent removal
  10. customafforded a crude oil which
  11. customwas purified on silica gel using 8:1:1 mixture of hexane

Sources & evidence

ORD record
ord-410acc0ad4a048879d6105580d543ac9
Source dataset
uspto-grants-1994_03
Patent number
US05292879

Reaction notes

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