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Sodium Hydroxide → 1H-Indole-5-acetic acid, 7-((2,2-dimethyl-1-oxopropyl)amino)-4,6-dimethyl-1-octyl-

HRID 1107968
Notes
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Reaction equation

HRID 1107968 reaction equation
[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([CH2:26][C:27]([O:29]CC)=[O:28])=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+]>CCO.O>[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([CH2:26][C:27]([OH:29])=[O:28])=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH:11]=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22247342N-(1-octyl-5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 158955711H-Indole-5-acetic acid, 7-((2,2-dimethyl-1-oxopropyl)amino)-4,6-dimethyl-1-octyl-Yield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

N-(1-Octyl-5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide (3.5 g) was dissolved in EtOH (50 ml), and a solution of NaOH (1.6 g) in water (20 ml) was added, which was followed by stirring at 60° C. for 1 hr. EtOH was evaporated under reduced pressure, and the residue was dissolved in water (20 ml), and washed with AcOEt (10 ml). The aqueous layer was neutralized with 2N HCl and extracted with AcOEt (50 ml). The AcOEt layer was washed successively with saturated brine and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure to give 2.0 g of the title compound.

Workup

  1. customEtOH was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water (20 ml)
  3. washwashed with AcOEt (10 ml)
  4. extractionextracted with AcOEt (50 ml)
  5. washThe AcOEt layer was washed successively with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAcOEt was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6192a32f71d64974953400b505162bf7
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06063806

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes