Hydrochloric Acid → 5-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxybenzoic Acid

HRID 17513Notes

Reaction equation

HRID 17513 reaction equation
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21].Cl>C1C=CC=CC=1.C(OCC)(=O)C>[Br:12][C:8]1[CH:9]=[C:10]([OH:11])[C:2]([NH:1][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 217551432-Amino-5-bromo-3-hydroxybenzoic Acid

Product 1

HCID 685848145-Bromo-2-(2,2-dimethylpropionylamino)-3-hydroxybenzoic AcidYield 98.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

2-Amino-5-bromo-3-hydroxybenzoic acid (I-219) (11.92 g, 51.37 mmol) was dissolved in benzene (360 ml), and pyridine (12.5 m, 154.12 mmol) and pivaloyl chloride (19.0 ml, 154.12 mmol) were added at room temperature. After stirred at 85° C. under nitrogen atmosphere for 3.5 hours, this was cooled to room temperature. The solution was fractionated with ethyl acetate and aqueous 1 M hydrochloric acid solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was subjected to column chromatography with silica gel, and the fraction with hexane:ethyl acetate=95:5 gave the entitled compound (15.98 g, 98.4%) as a brown solid.

Workup

  1. temperaturethis was cooled to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-cc29d5cd193d4f24af7263ab2dc7c705
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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