HCID 10593300, compound → 4,6-Dibromo-3-hydroxyanthranilic acid

HRID 1418530Notes

Reaction equation

HRID 1418530 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Br: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]([Br:11])[CH:10]=1)[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 10593300HCID 10593300, compound

Product 1

HCID 99048004,6-Dibromo-3-hydroxyanthranilic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,6-Dibromo-3-hydroxy-2-nitrobenzoic acid (4.09 g, 12 mmol) and PtS2 (160 mg, 0.62 mmol) in EtOH (150 mL) was hydrogenated at atmospheric pressure and room temperature for 45 h. Filtration and evaporation of the filtrate gave a crude product (3.69 g) which was purified by flash chromatography (SiO2, toluene-EtOAc). Treatment with activated charcoal in MeOH and crystallization from MeOH/H2O gave the title compound (2.51 g). Mp: 162°-164.5° C. 1H NMP (DMSO-d6): δ 6.96 (s, 1 H). 13C NMR (DMSO-d6): δ 167.69, 140.56, 139.95, 121.81, 117.23, 112.53, 110.45. MS(EI, 70ev): m/z (rel. int.) 309, 311, 313 (M+, 36, 72, 34).

Workup

  1. filtrationFiltration and evaporation of the filtrate
  2. customgave a crude product (3.69 g) which
  3. customwas purified by flash chromatography (SiO2, toluene-EtOAc)
  4. customTreatment with activated charcoal in MeOH and crystallization from MeOH/H2O

Sources & evidence

ORD record
ord-2a61951816b340d49ab2810df6f22d8b
Source dataset
uspto-grants-1999_03
Patent number
US05883129

Reaction notes

Loading…