Sodium Hydroxide → 3-[2-(4-Carboxyphenoxy)-ethyl]-2-(3-pyridyl)-indole

HRID 1980860Notes

Reaction equation

HRID 1980860 reaction equation
C([O:3][C:4]([C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>Cl>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]=2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:28][CH:29]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 204007903-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-indole

Product 1

HCID 204008143-[2-(4-Carboxyphenoxy)-ethyl]-2-(3-pyridyl)-indole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4.5 g of 3-[2-(4-ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-indole in 220 ml of 2N hydrochloric acid is heated under reflux for 6 hours. After cooling the solution is made basic with 3N NaOH and extracted with ethyl acetate. The basic solution is filtered and acidifed to pH 6-7 with 3N NCl. The solid is collected and dried to give 3-[2-(4-carboxyphenoxy)-ethyl]-2-(3-pyridyl)-indole.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling the solution
  4. extractionextracted with ethyl acetate
  5. filtrationThe basic solution is filtered
  6. customThe solid is collected
  7. customdried

Sources & evidence

ORD record
ord-fc974d9019c74f519b43c5ba1b849340
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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