Methanol → Methyl 3-aminophenylacetate

Participants

Reaction Steps

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.

Provenance & Evidence