Hydrochloric Acid → Ethyl 2-(3-aminophenoxy)acetate

HRID 1417993Notes

Reaction equation

HRID 1417993 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])([O-])=O.Cl>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2741030Ethyl 2-(3-nitrophenoxy)acetate

Product 1

HCID 412308Ethyl 2-(3-aminophenoxy)acetateYield 66%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-nitrophenoxyacetate (10 g) in ethanol (200 ml), iron powder (10 g) and concentrated hydrochloric acid (4.8 ml) was heated at reflux for 5 hours. The solid residue was removed by filtration whilst the mixture was hot, and was washed with warm ethanol. The solvent was evaporated and the residue partitioned between sodium bicarbonate solution and methylene chloride. The aqueous layer was separated and extracted with fresh methylene chloride. The combined organic extracts were dried (MgSO4) and evaporated. The residue was eluted through silica using a 5:3 mixture of hexane and ethyl acetate as eluent to give ethyl 3-aminophenoxyacetate as an orange oil in 66% yield;

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solid residue was removed by filtration whilst the mixture
  4. washwas washed with warm ethanol
  5. customThe solvent was evaporated
  6. customthe residue partitioned between sodium bicarbonate solution and methylene chloride
  7. customThe aqueous layer was separated
  8. extractionextracted with fresh methylene chloride
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. customevaporated
  11. washThe residue was eluted through silica using
  12. additiona 5:3 mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-c96e4611615e4631ad70946b96078b97
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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