Sodium Hydroxide → 3-Chloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetic acid

HRID 1372782Notes

Reaction equation

HRID 1372782 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([O:24]CC)=[O:23])[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)[N:13]([CH3:20])[CH:12]=1)=[O:10].[OH-].[Na+]>C1COCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[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)[N:13]([CH3:20])[CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17859282Ethyl 3-chloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetate

Product 1

HCID 178587693-Chloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetic acidYield 93.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (3-chloro-4-((1-methyl-3-indolylcarbonyl)amino)phenyl)acetate (639 mg, 1.72 mmol) was dissolved in THF (17.5 ml). To the resulting solution was added 0.25N NaOH (10.3 ml, 2.58 mmol), followed by stirring at room temperature for 4 hours. The reaction mixture was poured in 1N HCl (15 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (3-chloro-4-((1-methyl-3-indolylcarbonyl)amino)phenyl)acetic acid (549 mg, 93%) as a colorless 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-a93ee7d72e57489185cd74703a6983bc
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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