Nitric Acid → 5-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxy-6-nitrobenzoic acid

HRID 17514Notes

Reaction equation

HRID 17514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:18])[C:5]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:18])[C:5]([NH:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:14])[CH3:16])=[C:6]([C:10]=1[N+:19]([O-:21])=[O:20])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 685848145-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxybenzoic Acid

Product 1

HCID 866308645-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxy-6-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxybenzoic acid (I-220) was dissolved in acetic acid (3 ml), then fuming nitric acid (22 μl, 0.52 mmol) was added at room temperature. After stirring at room temperature for 1 hour, the solvent was evaporated away under reduced pressure. The residue was fractionated with ethyl acetate and saturated brine. The organic layer was again washed with saturated brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated away and the resulting residue was subjected to column chromatography with silica gel, and the fraction with hexane:ethyl acetate=3:1 gave 5-bromo-2-(2,2-dimethylpropionylamino)-3-hydroxy-6-nitrobenzoic acid (61 mg, 36) and the entitled compound (22 mg, 13%).

Workup

  1. customthe solvent was evaporated away under reduced pressure
  2. washThe organic layer was again washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-6ba6841b78714b57b1a9f8eb21bd0ae2
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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