Methanol → Methyl 2-(3-aminophenoxy)phenylacetate

HRID 1741878Notes

Reaction equation

HRID 1741878 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16])([O-])=O.CO>[Fe].C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 2

HCID 887MethanolHCID 15125766Methyl 2-(3-nitrophenoxy)phenylacetate

Product 1

HCID 15125767Methyl 2-(3-aminophenoxy)phenylacetateYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 2-(3-nitrophenoxy)phenylacetate (15 g), methanol (100 ml), glacial acetic acid (100 ml), and iron powder (15.0 g) was gently heated with stirring to reflux. After 30 minutes the mixture was cooled and the excess iron powder was filtered off. This filtrate was poured into water (700 ml) and extracted with ether (2×200 ml). The ether extracts were neutralized by stirring with aqueous sodium bicarbonate then dried, filtered and concentrated to give methyl 2-(3-aminophenoxy)phenylacetate (13.0 g, 97% yield) as a pale yellow oil.

Workup

  1. temperaturewas gently heated
  2. temperatureto reflux
  3. temperatureAfter 30 minutes the mixture was cooled
  4. filtrationthe excess iron powder was filtered off
  5. additionThis filtrate was poured into water (700 ml)
  6. extractionextracted with ether (2×200 ml)
  7. stirringby stirring with aqueous sodium bicarbonate
  8. customthen dried
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ca657badd23e4930987dbccdc9c0307d
Source dataset
uspto-grants-1994_08
Patent number
US05334748

Reaction notes

Loading…