Iodine → HCID 57771992, compound

HRID 1661908Notes

Reaction equation

HRID 1661908 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[NH2:12].[I:13]I>C(O)(=O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:13][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]([NH2:12])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 807IodineHCID 854916-Nitro-o-anisidine

Product 1

HCID 57771992HCID 57771992, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6.2 g (36.9 mmol) 2-methoxy-6-nitro-phenylamine, 9.4 g (37 mmol) iodine and 5.8 g (18.5 mmol) silver sulfate in 90 ml glacial acetic acid is stirred at 60° C. for 12 h. The reaction mixture is cooled to room temperature, poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1) to afford 8.57 g of the title compound as bright red crystals.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. additionpoured on water
  3. extractionextracted (3×) with ethyl acetate
  4. washThe combined organic layers are washed with water (2×) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1)

Sources & evidence

ORD record
ord-8bb99107c24d484ba80be0aa0c994b3f
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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