3,5-diiodonitrobenzene → 3,5-DIIODOANILINE

HRID 1657168Notes

Reaction equation

HRID 1657168 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-DIIODOANILINE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 61.5 G (0.164M) of 3,5-diiodonitrobenzene, from step (a), and 111.1 G (0.4924M) of stannous chloride in 900 ml of absolute ethanol was heated to reflux 1.5 hours under nitrogen. Most of the solvent was removed. The residue was stirred with ethylacetate, 5 normal sodium hydroxide and ice. Organic phase was separated and washed with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, solvent was removed to afford a crude oil, which was chromatographed on silica gel using 8:1:1 mixture of hexane:methylene chloride:ethyl acetate. The desired aniline was obtained as 35 G of light tan colored solid.

Workup

  1. temperatureto reflux 1.5 hours under nitrogen
  2. customMost of the solvent was removed
  3. customOrganic phase was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate, solvent
  6. customwas removed
  7. customto afford a crude oil, which
  8. customwas chromatographed on silica gel using 8:1:1 mixture of hexane

Sources & evidence

ORD record
ord-2304b7b89573467fbe4b84956bb03d49
Source dataset
uspto-grants-1993_10
Patent number
US05256777

Reaction notes

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