3-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indole → 3-(2-carboxyethyl)-N-(3-pyridyl)indole

HRID 485338Notes

Reaction equation

HRID 485338 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)=[O:5])C>CO.[OH-].[Na+]>[C:4]([CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 202701823-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indole

Product 1

HCID 134903533-(2-carboxyethyl)-N-(3-pyridyl)indole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.0 g of 3-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indole in 10 ml of methanol and 10 ml of 1N sodium hydroxide is refluxed for two hours, cooled, and evaporated. The residue is taken up in 10 ml of water, extracted with 10 ml of ether and adjusted to pH=6 with concentrated sulfuric acid. The resulting solid is filtered and dried to yield 3-(2-carboxyethyl)-N-(3-pyridyl)indole, m.p. 147°-149°.

Workup

  1. temperaturecooled
  2. customevaporated
  3. extractionextracted with 10 ml of ether
  4. filtrationThe resulting solid is filtered
  5. customdried

Sources & evidence

ORD record
ord-ee34d8fe9f954488bb4d46a25f795861
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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