Hydrochloric Acid → Methyl 2-amino-3,4-dimethoxybenzoate

HRID 1703396Notes

Reaction equation

HRID 1703396 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[NH2:15].[CH3:16]O>>[CH3:16][O:8][C:7](=[O:9])[C:6]1[C:5](=[C:4]([O:3][CH3:2])[C:12]([O:13][CH3:14])=[CH:11][CH:10]=1)[NH2:15]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 117455912-Amino-3,4-dimethoxybenzoic acid

Product 1

HCID 12919998Methyl 2-amino-3,4-dimethoxybenzoateYield 82%

Procedure

Hydrogen chloride was passed into a solution of 3,4-dimethoxyanthranilic acid (100 g., 0.51 mole) in 1.5 liters methanol for 40 minutes. The reaction mixture was refluxed for 4 days while introducing hydrogen chloride gas intermittently. The solvent was removed in vacuo, and the residual white solid was dissolved in 500 ml. water, cooled and basified to pH 10 with sodium hydroxide solution. After cooling for an additional hour, the cream color product (87.0 g., 82% yield) was filtered. Recrystallization from methanol furnished pure product, M.P. 66°-67° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 days
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residual white solid was dissolved in 500 ml
  4. temperaturewater, cooled
  5. temperatureAfter cooling for an additional hour
  6. filtrationthe cream color product (87.0 g., 82% yield) was filtered
  7. customRecrystallization from methanol furnished pure product, M.P. 66°-67° C.

Sources & evidence

ORD record
ord-48fde8aac4664456ad711eb67188607d
Source dataset
uspto-grants-1982_09
Patent number
US04351940

Reaction notes

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