Acetic Acid → 4-Amino-2-fluoro-3-methoxybenzoic acid

HRID 1880974Notes

Reaction equation

HRID 1880974 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([N+:12]([O-])=O)[CH:7]=[CH:6]C=1C#N.[H][H].[C:17]([OH:20])(=[O:19])[CH3:18]>OS(O)(=O)=O.O.CO>[NH2:12][C:8]1[CH:7]=[CH:6][C:18]([C:17]([OH:20])=[O:19])=[C:2]([F:1])[C:9]=1[O:10][CH3:11]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 579555492-Fluoro-3-methoxy-4-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 193583414-Amino-2-fluoro-3-methoxybenzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-fluoro-3-methoxy-4-nitrobenzonitrile (170 mg) in H2SO4 and H2O (0.5 mL/0.5 mL) was heated at 100° C. for 18 h. After which, it was separated between ethyl acetate and water. Organic extract was dried and concentrated to give a residue, which was then dissolved in a mixture of methanol and acetic acid (2 mL/2 mL) and was hydrogenated using hydrogen balloon overnight. The solution was filtered through celite, and the filtrate concentrated to give a read solid as the product. [M+H] calc'd for C8H8FNO3, 186; found 186.

Workup

  1. customAfter which, it was separated between ethyl acetate and water
  2. extractionOrganic extract
  3. customwas dried
  4. concentrationconcentrated
  5. customto give a residue, which
  6. filtrationThe solution was filtered through celite
  7. concentrationthe filtrate concentrated
  8. customto give a read solid as the product

Sources & evidence

ORD record
ord-769799971bf84eeea1706a67bb5eb0f4
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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