Potassium Hydroxide → HCID 21477014, compound

HRID 2293556Notes

Reaction equation

HRID 2293556 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[C:15](Cl)=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:17][CH3:18])[CH:8]=2)=[O:5])[CH2:3][CH2:2]1.[OH-].[K+].[H][H]>CO.[C].[Pd]>[CH:1]1([C:4]([NH:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:17][CH3:18])[CH:8]=2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 10754475HCID 10754475, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21477014HCID 21477014, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A 2.0 g portion of 4-cyclopropylcarbonylamino-5-chloro-2-methoxybenzoic acid and 856 mg of potassium hydroxide were dissolved in 30 ml of methanol, and 600 mg of 10% palladium-carbon powder was added, followed by stirring at room temperature for 9 hours in an atmosphere of hydrogen. The reaction solution was filtered, and the filtrate was concentrated under a reduced pressure, diluted with 1N hydrochloric acid aqueous solution and then extracted with chloroform. The organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. Then, the solvent was evaporated under a reduced pressure and the resulting residue was washed with diethyl ether to give 1.60 g of 4-cyclopropylcarbonylamino-2-methoxybenzoic acid.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. additiondiluted with 1N hydrochloric acid aqueous solution
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with water and saturated brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThen, the solvent was evaporated under a reduced pressure
  8. washthe resulting residue was washed with diethyl ether

Sources & evidence

ORD record
ord-8f3976b25bcd450baf1ce9992e937708
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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