Ethanol → HCID 22180284, compound

HRID 1836813Notes

Reaction equation

HRID 1836813 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.[CH2:18](O)[CH3:19]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH2:18][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 178233-Amino-4-methoxybenzoic acid

Product 1

HCID 22180284HCID 22180284, compoundYield 89.4%

Conditions

Temperature
65 °C

Procedure

3-Amino-4-methoxybenzoic acid (3.34 g) was dissolved in ethanol (100 ml). Concentrated sulfuric acid (3 ml) was added to the solution, and the mixture was stirred at 65° C. overnight. The solvent was removed from the reaction solution by distillation under the reduced pressure, and the residue was adjusted to pH 7 by the addition of a saturated aqueous sodium carbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 3.50 g (89.4%) of ethyl 3-amino-4-methoxybenzoate.

Workup

  1. customThe solvent was removed from the reaction solution by distillation under the reduced pressure
  2. additionthe residue was adjusted to pH 7 by the addition of a saturated aqueous sodium carbonate solution
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-aec4979eb38243e9954f9d936f6dc40b
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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