Ammonium Chloride → HCID 86714459, compound

HRID 2207476Notes

Reaction equation

HRID 2207476 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 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 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-b0157257c3774f47b0fb88bb322b5026
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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