4-Bromo-6-fluoro-3-hydroxy-2-nitrobenzoic acid → 4-Bromo-6-fluoro-3-hydroxyanthranilic acid
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
Product 1
Reagents, catalysts & solvents 1
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
- filtrationHydrogenation at room temperature and at atmospheric pressure for 14 h followed by filtration and evaporation
- customgave a crude product
- 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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