Water → Methyl 2-(3-amino-4-chlorophenoxy)acetate

HRID 1922084Notes

Reaction equation

HRID 1922084 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([N+:13]([O-])=O)[CH:7]=1.[Cl-].[NH4+].O.[OH-].[Na+]>CO.[Fe]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66717584HCID 66717584, compound

Product 1

HCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetateYield 53.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (4-chloro-3-nitrophenoxy)acetic acid methyl ester (30 g) in methanol (100 mL) was added to a mixture of iron (26 g), ammonium chloride (33 g) and water (400 mL) at room temperature, and the resulting mixture was heated in an ultrasonic bath at 60° C. for 4 hours. The mixture was basified by the addition of sodium hydroxide, extracted with ethyl acetate, and the combined extracts were washed with 1.0 M aqueous hydrochloric acid solution. The pH of the combined aqueous phases was adjusted to 7-8 by the addition of sodium hydroxide, and the resulting precipitate was collected by filtration and then dried to afford title compound (14 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe combined extracts were washed with 1.0 M aqueous hydrochloric acid solution
  3. additionThe pH of the combined aqueous phases was adjusted to 7-8 by the addition of sodium hydroxide
  4. filtrationthe resulting precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-c51ec571d6ad4edc8285349b51fc9796
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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