Methanol → Methyl 4-(aminomethyl)-2-fluorobenzoate

HRID 2411335Notes

Reaction equation

HRID 2411335 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:13])[CH:5]=1.S(=O)(=O)(O)O.[CH3:19]O>>[NH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:19])=[O:9])=[C:6]([F:13])[CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 71252304HCID 71252304, compound

Product 1

HCID 57572260Methyl 4-(aminomethyl)-2-fluorobenzoate

Procedure

4-Aminomethyl-2-fluorobenzoic acid hydrochloride (500 mg) was dissolved in methanol (10 mL), concentrated sulfuric acid (6 μL) was added, and the mixture was stirred with heating under reflux for 9 hr. After completion of the reaction, the solvent was evaporated, saturated aqueous potassium carbonate solution was added, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and the solvent was evaporated to give the title compound (181 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 9 hr
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. additionsaturated aqueous potassium carbonate solution was added
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4204203f8c4e4ce28a0b5967653ef45d
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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