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

HRID 1372635Notes

Reaction equation

HRID 1372635 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

To a solution of ethyl 3-chloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetate (639 mg, 1.72 mmol) in THF (17.5 mL) was added 0.25N NaOH (10.3 mL, 2.58 mmol). The resulting mixture was stirred at room temperature for 4 hours. Under ice cooling, the reaction mixture was poured in 1N HCl (15 ml). The crystals thus precipitated were collected by filtration, washed with water and dried under reduced pressure, whereby 3-chloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetic acid (549 mg, 93%) was obtained as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-7410b1fa0c4c4911a05df6ebc21f9460
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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