Methanol → Methyl 3-Amino-4-methoxybenzoate

HRID 1776531Notes

Reaction equation

HRID 1776531 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178233-Amino-4-methoxybenzoic acid

Product 1

HCID 2734814Methyl 3-Amino-4-methoxybenzoateYield 94%

Procedure

A mixture of 3-amino-4-methoxybenzoic acid (0.500 g, 2.99 mmol) and a catalytic amount of aqueous conc. sulfuric acid in MeOH (30 ml) was heated to reflux for 48 hours. The solvent was removed, and the crude was portioned between EtOAc and NaHCO3 5%. The organic phase was dried over Na2SO4 and the solvent was removed affording methyl 3-amino-4-methoxybenzoate (0.509 g, 2.81 mmol, 94% yield, MS/ESI+ 181.9 [MH]+). This product was used without purification.

Workup

  1. temperatureto reflux for 48 hours
  2. customThe solvent was removed
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-4c0600bfac5f4767ba06bb5bbb38820f
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…