Ammonium Chloride → HCID 118005911, compound

HRID 1049617Notes

Reaction equation

HRID 1049617 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:3]=1.[NH4+].[Cl-]>CCO.[Fe]>[I:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:3]=1)[NH2:8]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 118006083HCID 118006083, compound

Product 1

HCID 118005911HCID 118005911, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

7 (4.9 g, 13 mmol), Fe (5.9 g, 100 mmol) and a solution of NH4Cl (2.3 g in 23 mL H2O, 42 mmol) were suspended in 67 mL of EtOH and heated at 75° C. for 6 h. The mixture was allowed to cool to room temperature, filtered over celite, and concentrated by rotary evaporation. The residue was partitioned between EtOAc and water; combined organic extracts were dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 3-iodo-5-(2-methoxyphenoxy)aniline (8) (3.4 g, 77%). 1H NMR (600 MHz, CDCl3) δ 7.18-7.13 (m, 1H), 7.00 (ddd, J=7.7, 5.7, 1.5 Hz, 2H), 6.94 (td, J=7.7, 1.4 Hz, 1H), 6.83-6.79 (m, 1H), 6.71-6.68 (m, 1H), 6.30 (t, J=2.0 Hz, 1H), 3.82 (s, 3H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered over celite
  3. concentrationconcentrated by rotary evaporation
  4. customThe residue was partitioned between EtOAc and water
  5. dry with materialcombined organic extracts were dried over anhydrous Na2SO4
  6. concentrationconcentrated by rotary evaporation
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-22e353538d8242909bb3cbf23cc20489
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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