Hydrochloric Acid → Methyl 2-amino-5-methoxybenzoate

HRID 2373351

Reaction equation

HRID 2373351 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[CH3:14]O>>[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([O:7][CH3:14])=[O:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2779305-Methoxyanthranilic acid

Product 1

HCID 13052275Methyl 2-amino-5-methoxybenzoate

Conditions

Temperature
60 °C

Procedure

Hydrogen chloride gas was bubbled through a solution of 2-amino-5-methoxybenzoic acid (5.0 g, 30 mmol) in MeOH (200 mL) for 30 minutes. The solution was heated at 60° C. overnight. The reaction was cooled and the solvent removed in vacuo. The residue was dissolved in water, basified with 5M NaOH and extracted twice with ether. The ether extracts were washed with 5M NaOH and water, dried (MgSO4), filtered and concentrated in vacuo to give i-e (4.25 g, 78%): MS m/z═182 (M+H).

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted twice with ether
  5. washThe ether extracts were washed with 5M NaOH and water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give i-e (4.25 g, 78%)

Sources & evidence

ORD record
ord-485b0003c27d4732bd3d76857f9246f2
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Linked notes

Loading…