Potassium Hydroxide → N-[3-(2-carboxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide

HRID 1531976Notes

Reaction equation

HRID 1531976 reaction equation
C([N:4]1[C:12]2[C:7](=[C:8]([CH3:21])[CH:9]=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]([CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])[CH2:5]1)(=O)C.[OH-].[K+]>CCO.O>[C:24]([CH2:23][CH2:22][CH:6]1[C:7]2[C:12](=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])[C:10]([CH3:20])=[CH:9][C:8]=2[CH3:21])[NH:4][CH2:5]1)([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22247307N-[1-Acetyl-3-(2-ethoxycarbonylethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide

Product 1

HCID 22247340N-[3-(2-carboxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamideYield 70.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[1-Acetyl-3-(2-ethoxycarbonylethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide (2.6 g) was dissolved in EtOH (40 ml), and a solution of KOH (1.3 g) in water (10 ml) was added, which was followed by refluxing for 20 hr. EtOH was evaporated under reduced pressure, and the mixture was adjusted to pH 5 with 2N hydrochloric acid and extracted with CHCl3 (100 ml). The CHCl3 layer was washed with water and dried over anhydrous sodium sulfate, CHCl3 was evaporated under reduced pressure to give 1.5 g of N-[3-(2-carboxyethyl)-4,6-dimethylindolin-7-yl]-2,2-dimethylpropanamide. 1H-NMR (CDCl3) δ

Workup

  1. temperatureby refluxing for 20 hr
  2. customEtOH was evaporated under reduced pressure
  3. extractionextracted with CHCl3 (100 ml)
  4. washThe CHCl3 layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate, CHCl3
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-2d46928d0ce64f61b93f623c8d0bc73b
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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