Hydrochloric Acid → 4-Amino-2-fluoro-3-methylbenzoic acid

HRID 377275Notes

Reaction equation

HRID 377275 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[C:4]([F:13])[C:3]=1[CH3:14].[OH-].[Na+].Cl>C(O)C>[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:13])[C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19358316Ethyl 4-amino-2-fluoro-3-methylbenzoate

Product 1

HCID 193583204-Amino-2-fluoro-3-methylbenzoic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 7 ml of ethanol was suspended 0.70 g of ethyl 4-amino-2-fluoro-3-methylbenzoate, followed by adding thereto 7 ml of lN sodium hydroxide, and the resulting mixture was stirred at 40° C. for 4 hours. To the reaction mixture was added 1.2 ml of 6N hydrochloric acid, followed by extraction with 50 ml of ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent, to obtain 0.59 g of 4-amino-2-fluoro-3-methylbenzoic acid as colorless crystals.

Workup

  1. additionby adding
  2. extractionfollowed by extraction with 50 ml of ethyl acetate
  3. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-eb8017b3b8a348f08efb059870b50d3e
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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