4-Bromo-6-fluoro-3-hydroxy-2-nitrobenzoic acid → 4-Bromo-6-fluoro-3-hydroxyanthranilic acid

HRID 1418541Notes

Reaction equation

HRID 1418541 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-])=O)[C:3]=1[OH:15]>CCO>[Br:1][C:2]1[C:3]([OH:15])=[C:4]([NH2:12])[C:5](=[C:9]([F:11])[CH:10]=1)[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 541626324-Bromo-6-fluoro-3-hydroxy-2-nitrobenzoic acid

Product 1

HCID 543129384-Bromo-6-fluoro-3-hydroxyanthranilic acidYield 2.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-6-fluoro-3-hydroxy-2-nitrobenzoic acid (22 mg 0.78 mmol) was dissolved in EtOH (10 mL) and PtS2 (2 mg) was added. Hydrogenation at room temperature and at atmospheric pressure for 14 h followed by filtration and evaporation gave a crude product. Purification by flash chromatography (SiO2, toluene-EtOAc-HOAc) afforded the product (4 mg). 1H NMR (CD3OD): δ 6.44 (d, J=11.3 Hz, 1 H); MS (EI, 70 eV): m/z (rel. int.) 249/251 (M+, 93/90).

Workup

  1. filtrationHydrogenation at room temperature and at atmospheric pressure for 14 h followed by filtration and evaporation
  2. customgave a crude product
  3. customPurification by flash chromatography (SiO2, toluene-EtOAc-HOAc)

Sources & evidence

ORD record
ord-d24960f8c5c84190b2d2d84c6fe231ff
Source dataset
uspto-grants-1999_03
Patent number
US05883129

Reaction notes

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