Sodium Hydroxide → HCID 17858818, compound

HRID 1372686Notes

Reaction equation

HRID 1372686 reaction equation
[Br: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>[Br: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]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58778971HCID 58778971, compound

Product 1

HCID 17858818HCID 17858818, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (3-bromo-4-((3-indolylcarbonyl)amino)phenyl)acetate (664 mg, 1.65 mmol) was dissolved in THF (17 ml). To the resulting solution was added 0.25N NaOH (10.0 ml, 2.48 mmol). After stirring at room temperature for 24 hours, the reaction mixture was poured in 1N HCl to acidify the mixture. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water, and dried under reduced pressure to give (3-bromo-4-((3-indolylcarbonyl)amino)phenyl)acetic acid (341 mg, 55%) as a brown solid.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration under reduced pressure
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-e38c5c1052a44b5f9f82ce1c001a213b
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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