HCID 20270201, compound → HCID 20270193, compound

HRID 485364Notes

Reaction equation

HRID 485364 reaction equation
C([O:3][C:4]([C:6]1[CH:28]=[CH:27][C:9]([O:10][CH2:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:13]=2)=[CH:8][CH:7]=1)=[O:5])C>C(O)C.[OH-].[Na+]>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:13]=2)=[CH:27][CH:28]=1)([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 20270201HCID 20270201, compound

Product 1

HCID 20270193HCID 20270193, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of crude 3-[(p-ethoxycarbonylphenoxy)methyl]-N-(3-pyridyl)-indole (6.5 g) in 60 ml of ethanol and 60 ml of 1N sodium hydroxide is heated under reflux for 3 hours. The ethanol is distilled off, the aqueous phase is washed with ether, acidified with conc. hydrochloric acid to pH=6, and the resulting solid is filtered off to yield 3-[(p-carboxyphenoxy)-methyl]-N-(3-pyridyl)indole. Treatment with ethanolic hydrogen chloride gives 3-[(p-carboxyphenoxy)methyl]-N-(3-pyridyl)indole hydrochloride.

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationThe ethanol is distilled off
  3. washthe aqueous phase is washed with ether
  4. filtrationthe resulting solid is filtered off

Sources & evidence

ORD record
ord-380751b63ba0458eaef47a49bf482ed6
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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