Ethyl 4-chlorobenzoate → HCID 13393254, compound

HRID 2309243Notes

Reaction equation

HRID 2309243 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.CC[O-].[Na+].Cl.[NH2:18][CH:19]([CH2:23][CH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][C:25]1=[O:33])[C:20]([OH:22])=[O:21]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:18][CH:19]([CH2:23][CH:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:26][C:25]2=[O:33])[C:20]([OH:22])=[O:21])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 81785Ethyl 4-chlorobenzoateHCID 2723922Sodium ethoxideHCID 133932472-Amino-3-(2-oxoindolin-3-yl)propanoic acid hydrochloride

Product 1

HCID 13393254HCID 13393254, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 100 ml of ethanol, 1.66 g of ethyl p-chlorobenzoate, 0.5 g of sodium ethylate and 1.98 g of 2-amino-3-(oxindol-3-yl)propionic acid hydrochloride prepared in Reference example 1 were added, then the mixture was placed in an autoclave, and reacted under 110 atmospheric pressure at 140°-150° C. for 6 hours. After cooling, the reaction mixture was concentrated under a reduced pressure, the residue was dissolved in 200 ml of chloroform, then the chloroform solution was washed with 1% potassium carbonate aqueous solution, diluted hydrochloric acid and water in this order, the chloroform solution was dried with anhydrous sodium sulfate. The solvent was removed by evaporation, the residue was recrystallized from methanol-water to obtain 270 mg of 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionic acid 1/4-hydrate in the form of colorless powdery substance. Melting point: 133-135° C. [α]D25 -50.3° (C=1, methanol)

Workup

  1. additionwere added
  2. customreacted under 110 atmospheric pressure at 140°-150° C. for 6 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under a reduced pressure
  5. dissolutionthe residue was dissolved in 200 ml of chloroform
  6. washthe chloroform solution was washed with 1% potassium carbonate aqueous solution, diluted hydrochloric acid and water in this order
  7. dry with materialthe chloroform solution was dried with anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation
  9. customthe residue was recrystallized from methanol-water

Sources & evidence

ORD record
ord-f20c269618634eb28d7defb1578ecbce
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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