Water → 3-Iodo-4-(2-methoxyethoxy)aniline

HRID 1593766Notes

Reaction equation

HRID 1593766 reaction equation
[Cl-].[NH4+].O.[I:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:6]=1[O:14][CH2:15][CH2:16][O:17][CH3:18]>C(O)C.[Fe]>[I:4][C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:6]=1[O:14][CH2:15][CH2:16][O:17][CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 69310862HCID 69310862, compound

Product 1

HCID 660942063-Iodo-4-(2-methoxyethoxy)anilineYield 58.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A suspension of iron (3.89 g, 69.7 mmol), ammonium chloride (5.0 g, 93.5 mmol), in 100 mL of ethanol and 28 mL of water was heated to reflux. 2-Iodo-1-(2-methoxyethoxy)-4-nitrobenzene (7.5 g, 23.2 mmol) was added and the reaction was heated at reflux for 3 hours. The mixture was cooled to room temperature and filtered through Celite, washed with ethanol. The filtrate was concentrated in vacuo until a precipitate appeared. The precipitate was removed by filtration through Magnesol and the filtrate was concentrated in vacuo to provide 4.0 g of [3-iodo-4-(2-methoxyethoxy)phenyl]amine as an oil; 1H NMR (300 MHz, DMSO-d6) δ 3.33 (s, 3H), 3.62 (t, 2H), 3.95 (t, 2H), 5.01 (d, 2H), 6.55 (d, 1H), 6.73 (d, 1H), 7.03 (s, 1H); MS (ES) m/z294.0 (M+H)

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered through Celite
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated in vacuo until a precipitate
  6. customThe precipitate was removed by filtration through Magnesol
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b1267d0101b0479ba5b1f6cb26cf075d
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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