Sodium Hydroxide → 4-[[(2,3-Dihydro-2-oxo-1H-indol-5-yl)amino]carbonyl]benzoic acid

HRID 428263Notes

Reaction equation

HRID 428263 reaction equation
C[O:2][C:3]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH2:15]3)=[O:10])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH2:15]3)=[O:10])=[CH:22][CH:23]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 232899625-(4-Methoxycarbonylbenzamido)-2-oxindole

Product 1

HCID 232899584-[[(2,3-Dihydro-2-oxo-1H-indol-5-yl)amino]carbonyl]benzoic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Methoxycarbonylbenzamido)-2-oxindole (0.9 g) and 0.4 g of sodium hydroxide in 25 mL of methanol were refluxed for 3 hours. The mixture was concentrated, water added, and the mixture acidified with 6N hydrochloric acid. The precipitate was collected by vacuum filtration to give 0.75 g (87%) of the title compound as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater added
  3. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-4ca912c5d1d34ecea4526cab00056225
Source dataset
uspto-grants-2001_11
Patent number
US06313158B1

Reaction notes

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