Methanol → Methyl 3-aminophenylacetate

HRID 1623668Notes

Reaction equation

HRID 1623668 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH3:17]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 13054266Methyl 3-aminophenylacetate

Procedure

A mixture of (3-aminophenyl)acetic acid (5.0 g, 33 mmol), methanol (150 ml), and c.H2SO4 (10 ml) was heated at reflux overnight. The solvent was evaporated in vacuo and the residue taken up in water (50 ml) and ethyl acetate (200 ml). Solid Na2CO3 was added until the solution was pH 10. The layers were separated and the aqueous layer was extracted again with ethyl acetate (250 ml). The organic layers were combined, washed with brine, dried (MgSO4) and evaporated in vacuo to give the title compound as a brown oil. 5.0 g.

Workup

  1. temperatureat reflux overnight
  2. customThe solvent was evaporated in vacuo
  3. additionSolid Na2CO3 was added until the solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted again with ethyl acetate (250 ml)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-7af02d947aec4876aa7c6294a42a9d79
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…