Ammonium Chloride → Methyl 2-(4-amino-2-chlorophenyl)acetate

HRID 2077768Notes

Reaction equation

HRID 2077768 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13].[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21876245Methyl 2-(2-chloro-4-nitrophenyl)acetate

Product 1

HCID 21876454Methyl 2-(4-amino-2-chlorophenyl)acetateYield 83.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of methyl 2-(2-chloro-4-nitrophenyl)acetate (step 3, 3.6 g, 15.6 mmol) in ethanol/water (4/1) were added Fe (4.4 g, 78.0 mmol) and NH4Cl (409 mg, 7.8 mmol). The mixture was stirred for 1 h under reflux temperature. The solvent was removed and the residue was diluted with CH2Cl2. The mixture was washed with brine, dried (MgSO4) and concentrated to give 2.59 g (83%) of title compound as orange oil.

Workup

  1. temperatureunder reflux temperature
  2. customThe solvent was removed
  3. additionthe residue was diluted with CH2Cl2
  4. washThe mixture was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-774cfaa8664440488ddc621339aadffc
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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