Sodium Carbonate → 2-(Benzamido)-4-(3-methoxyphenyl)benzoic acid

HRID 1673369Notes

Reaction equation

HRID 1673369 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:18]([NH:26][C:27]1[CH:36]=[C:35](Br)[CH:34]=[CH:33][C:28]=1[C:29]([O:31]C)=[O:30])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C(=O)C>[C:18]([NH:26][C:27]1[CH:36]=[C:35]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:34]=[CH:33][C:28]=1[C:29]([OH:31])=[O:30])(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 57879335Methyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 578795042-(Benzamido)-4-(3-methoxyphenyl)benzoic acidYield 24.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

36 mg of 3-methoxyphenylboronic acid, 55 mg of sodium carbonate and 30 mg polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of methyl 2-(benzamido)-4-bromobenzoate, and stirred at 90° C. for 11 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.2 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and one solvent was evaporated under reduced pressure, 1.0 mL of 1.0 mol/L aqueous sodium hydroxide and 2.0 mL of ethanol were added to the obtained residue and stirred at room temperature for 1 hour. 0.6 mol/L hydrochloric acid was added to the reaction mixture and a solid substance was separated by filtration to obtain 18 mg of 2-(benzamido)-4-(3-methoxyphenyl)benzoic acid as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. custominsoluble were removed by filtration and ethyl acetate and 1.2 mol/L hydrochloric acid
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with 1.0 mol/L hydrochloric acid
  7. customa saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and one solvent was evaporated under reduced pressure, 1.0 mL of 1.0 mol/L aqueous sodium hydroxide and 2.0 mL of ethanol
  8. additionwere added to the obtained residue
  9. stirringstirred at room temperature for 1 hour
  10. addition0.6 mol/L hydrochloric acid was added to the reaction mixture
  11. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-ab76c2b6c4704b6ea00b7b6914f4b667
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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