Sodium Hydroxide → HCID 18976147, compound

HRID 2393603Notes

Reaction equation

HRID 2393603 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[C:5]([NH:7][C:8]1([CH2:23][CH2:24][C:25]([O:27]C)=[O:26])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[Cl:32])[C:5]([NH:7][C:8]1([CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]1=[O:22])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9847874HCID 9847874, compound

Product 1

HCID 18976147HCID 18976147, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.89 g of methyl 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]propionate, 16 ml of a 2N sodium hydroxide aqueous solution and 100 ml of methanol was refluxed for 40 minutes. After the reaction mixture was cooled to room temperature, the solvent was removed by evaporation under reduced pressure. The residue was diluted with water, adjusted to pH 4 with 10% hydrochloric acid and then extracted with chloroform. After the extract was washed with water and dried, the solvent was removed by evaporation. The resulting crude crystals were recrystallized from ethyl acetate-hexane to afford 3.34 g of 3-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]propionic acid as colorless crystals. Melting point: 202° to 204° C., IR (Nujol) (cm-1): 3260, 1730, 1675, 1660, FAB-MS (m/z): 463 (MH+), 173 (base).

Workup

  1. temperaturewas refluxed for 40 minutes
  2. customthe solvent was removed by evaporation under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with chloroform
  5. washAfter the extract was washed with water
  6. customdried
  7. customthe solvent was removed by evaporation
  8. customThe resulting crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8218776aab8d498cb753ad98ad3031de
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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