Methanol → Methyl 2-(3-aminophenoxy)phenylacetate

HRID 129599Notes

Reaction equation

HRID 129599 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-0136030c70164c4c82e1a351636f94b5
Source dataset
uspto-grants-1995_11
Patent number
US05468857

Reaction notes

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