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

HRID 858502Notes

Reaction equation

HRID 858502 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-4e87ca1bde444ebda14b631ee847ce0b
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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