Sodium Hydroxide → 4-Amino-2-fluoro-5-methoxybenzoic acid

HRID 219867Notes

Reaction equation

HRID 219867 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([F:14])[CH:3]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57955533Methyl 4-amino-2-fluoro-5-methoxybenzoate

Product 1

HCID 529829634-Amino-2-fluoro-5-methoxybenzoic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-amino-2-fluoro-5-methoxybenzoate (100 mg; 0.50 mmol; 1 eq.) was dissolved in MeOH (2 mL). NaOH (0.50 mL; 5 M; 2.51 mmol; 5 eq.) was added and the mixture was heated at 50° C. overnight. The solvents were evaporated. EtOAc was added and the resulting solution was washed with NH4Cl sat. The aqueous phase was extracted with EtOAc. Combined organic phases were dried over MgSO4, filtrated and evaporated, affording the title compound (92 mg; 99%). HPLC (Method A) Rt 1.92 min (Purity: 96.4%).

Workup

  1. customThe solvents were evaporated
  2. additionEtOAc was added
  3. washthe resulting solution was washed with NH4Cl sat. The aqueous phase
  4. extractionwas extracted with EtOAc
  5. dry with materialCombined organic phases were dried over MgSO4
  6. filtrationfiltrated
  7. customevaporated

Sources & evidence

ORD record
ord-6d045645d8c14478a243487d3d7f4dfc
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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