Ammonium Chloride → HCID 86714459, compound

HRID 409045Notes

Reaction equation

HRID 409045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[O:18][CH3:19])=[CH:4][C:3]=1[Cl:20].[Cl-].[NH4+]>O1CCCC1.O.[Fe]>[Cl:20][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[Cl:1])[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 71015399HCID 71015399, compound

Product 1

HCID 86714459HCID 86714459, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1,2-dichloro-4-(2-methoxy-4-nitrophenoxy)benzene (60 g, 190.40 mmol, 1.00 equiv), Fe (53 g, 946.43 mmol, 4.97 equiv) and ammonium chloride (10 g, 188.68 mmol, 0.99 equiv) in tetrahydrofuran/water (1/2) (600 mL) was stirred overnight at 60° C. under an inert atmosphere of nitrogen. The mixture was filtered through Celite and the filtrate was concentrated under vacuum. The resulting solution was extracted with 3×500 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 3×500 mL of brine. The mixture was dried over anhydrous magnesium sulfate and concentrated under vacuum to give 40 g (74%) of 4-(3,4-dichlorophenoxy)-3-methoxyaniline as a light gray solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. extractionThe resulting solution was extracted with 3×500 mL of dichloromethane
  4. washThe resulting mixture was washed with 3×500 mL of brine
  5. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-65f208fe0967414284d7930f0e35dc84
Source dataset
uspto-grants-2014_06
Patent number
US08759358B1

Reaction notes

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