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Sodium Hydroxide → 3-chloro-4-(N-(3-indolylcarbonyl)amino)phenylacetic acid

HRID 1372600
Notes
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Reaction equation

HRID 1372600 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([O:23]CC)=[O:22])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:10].[OH-].[Na+]>C1COCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([OH:23])=[O:22])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17858762Ethyl 3-chloro-4-(3-indolylcarbonylamino)phenylacetate

Product 1

HCID 178594403-chloro-4-(N-(3-indolylcarbonyl)amino)phenylacetic acidYield 91.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-chloro-4-(3-indolylcarbonylamino)phenylacetate (1.25 g, 3.50 mmol) in THF (35 mL) was added 0.25N NaOH (21 mL, 5.23 mmol) under stirring. The reaction mixture was then stirred at room temperature for 24 hours. The reaction mixture was poured in 1N HCl (30 ml) under stirring at 0° C. The crystals thus precipitated were collected by filtration, whereby 3-chloro-4-(N-(3-indolylcarbonyl)amino)phenylacetic acid (1.05 g, 91%) was obtained as a colorless solid.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 24 hours
  2. stirringunder stirring at 0° C
  3. customThe crystals thus precipitated
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-14359ea9a84e4d1d86fbeea32e6294f6
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07157487B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes