Ammonium Chloride → 4-Ethoxy-3-iodo-benzenamine

HRID 1593764Notes

Reaction equation

HRID 1593764 reaction equation
[Cl-].[NH4+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[I:15])[CH3:4]>C(O)C.O.[Fe]>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[I:15])[CH3:4]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 574195081-Ethoxy-2-iodo-4-nitrobenzene

Product 1

HCID 574195094-Ethoxy-3-iodo-benzenamineYield 96.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of iron (3.81 g, 70 mmol) and ammonium chloride (5.47 g, 102 mmol) in 80 mL of ethanol and 25 mL of water was heated to reflux. 1-Ethoxy-2-iodo-4-nitrobenzene (5.0 g, 20 mmol) was added in portions and the reaction was heated at reflux for 1 hour. The hot mixture was filtered through Celite, washed with hot ethanol. The filtrate was concentrated in vacuo and treated with ethyl acetate and water. The organic layer was extracted, washed with brine, dried over magnesium sulfate and filtered. Removal of the solvent in vacuo provided 5.1 g of (4-ethoxy-3-iodophenyl)amine as a light brown oil; 1H NMR (400 MHz, DMSO-d6) δ 1.30 (s, 3H), 3.89 (q, 2H), 4.82 (bs, 2H), 6.53 (dd, 1H), 6.72 (d, 1H), 7.11 (d, 1H); MS (ES) m/z263.9 (M+H)+

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 1 hour
  4. filtrationThe hot mixture was filtered through Celite
  5. washwashed with hot ethanol
  6. concentrationThe filtrate was concentrated in vacuo
  7. additiontreated with ethyl acetate and water
  8. extractionThe organic layer was extracted
  9. washwashed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-b4cd80198923468c96464ebec9a3cf44
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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