Methanol → Methyl 3-Amino-4-methoxybenzoate

HRID 349466

Reaction equation

HRID 349466 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].OS(O)(=O)=O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([NH2:1])[CH:3]=1

Participants

4

Reactant 3

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

Product 1

HCID 2734814Methyl 3-Amino-4-methoxybenzoateYield 90%

Procedure

3-amino-4-methoxy benzoic acid (40 g, 0.239 mol) was dissolved in methanol, H2SO4 (38.14 ml, 0.717 mol) was added dropwise thereto and refluxed for 12 hours. The resulting mixture was cooled to room temperature and concentrated under a reduced pressure to remove methanol, neutralized with NaHCO3, extracted with ethyl acetate, and the extract was concentrated under a reduced pressure. The resulting residue was purified by recrystallization from ethyl acetate/hexane to obtain the title compound (39 g, 0.215 mol) in a yield of 90%.

Workup

  1. temperaturerefluxed for 12 hours
  2. concentrationconcentrated under a reduced pressure
  3. customto remove methanol
  4. extractionextracted with ethyl acetate
  5. concentrationthe extract was concentrated under a reduced pressure
  6. customThe resulting residue was purified by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-56b670bf3a344ba1ad9a3b62c234d033
Source dataset
uspto-grants-2007_02
Patent number
US07179832B2

Linked notes

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