Methanol → Methyl 3-Amino-4-methoxybenzoate

HRID 1387528Notes

Reaction equation

HRID 1387528 reaction equation
OS(O)(=O)=O.[NH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:10]([OH:12])=[O:11].[CH3:18]O>>[CH3:18][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:7]([NH2:6])[CH:8]=1

Participants

4

Reactant 3

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

Product 1

HCID 2734814Methyl 3-Amino-4-methoxybenzoate

Procedure

Concentrated H2SO4 (9 mL) was added in portions to a stirred solution of 3-amino-4-methoxybenzoic acid (20.06 g, 110.4 mmol) in methanol (280 mL). The mixture was heated to reflux overnight then cooled to room temperature, and the solvent was removed in vacuo. The residue was shaken with 10% aqueous potassium carbonate then extracted with ethyl acetate three times. The combined extracts were washed with saturated sodium bicarbonate, dried (MgSO4), filtered, and stripped of solvent under reduced pressure. The residual solid was triturated with hexane and filtered to yield the product (10.82 g); m.p. 75-77° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed in vacuo
  4. extractionthen extracted with ethyl acetate three times
  5. washThe combined extracts were washed with saturated sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe residual solid was triturated with hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2f278032480049e982f4bdc353145190
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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