Acetic Acid → 2-Iodo-4-methoxyphenylamine

HRID 541904

Reaction equation

HRID 541904 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([I:12])[CH:4]=1.C(O)(=O)C>CO.O.[Fe]>[I:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH2:9]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 27334564-Nitro-3-iodoanisole

Product 1

HCID 110103362-Iodo-4-methoxyphenylamineYield 90%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 3-iodo-4-nitrophenyl methyl ether (5.0 g, 0.018 mol) in methanol (50 mL), water (5 mL), and acetic acid (10 mL) was added iron (3.00 g, 0.0538 mol) powder in small quantities. When the addition was completed, the reaction mixture was heated at 70° C. overnight. After filtration, the cake was rinsed with EtOAc. The filtrate was concentrated and the residue was diluted with NaHCO3 (aq) and EtOAc. After layer separation, the organic layer was dried, filtered and concentrated to give the desired product (4.0 g, 90%).

Workup

  1. additionWhen the addition
  2. filtrationAfter filtration
  3. washthe cake was rinsed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was diluted with NaHCO3 (aq) and EtOAc
  6. customAfter layer separation
  7. customthe organic layer was dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-83834a3d830940cea459d854688122b5
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

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