Hydrochloric Acid → Methyl (3-amino-4-chlorophenyl)acetate

HRID 1244673Notes

Reaction equation

HRID 1244673 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-])=O.Cl>CO.[Zn]>[NH2:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12069505HCID 12069505, compound

Product 1

HCID 21920780Methyl (3-amino-4-chlorophenyl)acetateYield 88.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

13.07 mmol (3.0 g) of methyl 4-chloro-3-nitrobenzeneacetate and 198.8 mmol (13.0 g) of Zn dust are refluxed in 500 ml of MeOH for 10 minutes. Then, 13 ml of concentrated HCl is added in drops under reflux and refluxed for another 30 minutes. The suspension is hot-filtered, the methanol is distilled off, and the residue is set at pH 14 with NaHCO3 solution. Extraction with ethyl acetate, drying with Na2SO4 and distillation of the solution yields 2.3 g of methyl 3-amino-4-chlorobenzeneacetate as a beige solid.

Workup

  1. temperatureunder reflux
  2. temperaturerefluxed for another 30 minutes
  3. filtrationThe suspension is hot-filtered
  4. distillationthe methanol is distilled off
  5. extractionExtraction with ethyl acetate
  6. dry with materialdrying with Na2SO4 and distillation of the solution

Sources & evidence

ORD record
ord-24e5b6f4a4904db7aefe4a881f56ccf0
Source dataset
uspto-grants-2006_10
Patent number
US07122570B2

Reaction notes

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