Hydrochloric Acid → HCID 13559602, compound

HRID 2309250Notes

Reaction equation

HRID 2309250 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][CH:9]([CH2:14][C:15]2([CH3:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:24])[C:10]([O:12]C)=[O:11])=[O:7])=[CH:4][CH:3]=1.Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([CH2:14][C:15]2([CH3:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]2=[O:24])[C:10]([OH:12])=[O:11])=[O:7])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13559601HCID 13559601, compound

Product 1

HCID 13559602HCID 13559602, compound

Procedure

2.9 Grams of methyl 2-(4-chlorobenzoylamino)-3-(3-methyloxindol-3-yl)propionate prepared in Example 48 was added to 10 ml of 10%-hydrochloric acid and the mixture was refluxed for 3 hours. After cooling, the reaction mixture was extracted with chloroform, the extract was washed with water and dried with anhydrous magnesium sulfate. The solvent was removed by evaporation, the residue was dissolved in a saturated sodium bicarbonate aqueous solution, then the resulting solution was filtered with Celite (trademark for diatomaceous earth product manufactured by Johns-Manville Products Corp.) as a filter aid. The filtrate was acidified with 10%-hydrochloric acid, the crystals formed were collected by filtration to obtain 230 mg of 2-(4-chlorobenzoylamino)-3-(3-methyloxindol-3-yl)propionic acid in the form of white powdery substance.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with chloroform
  4. washthe extract was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation
  7. dissolutionthe residue was dissolved in a saturated sodium bicarbonate aqueous solution
  8. filtrationthe resulting solution was filtered with Celite (trademark for diatomaceous earth product manufactured by Johns-Manville Products Corp.) as a filter aid
  9. customthe crystals formed
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-2bc903629ca546208405946ed02ee0ee
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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