3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole → 3-(1-oxo-4-carboxybutyl)-N-(3-pyridyl)-indole

HRID 64679Notes

Reaction equation

HRID 64679 reaction equation
[O:1]=[C:2]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8]CC)=[O:7]>[OH-].[Na+]>[O:1]=[C:2]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 136726963-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole

Product 1

HCID 136726973-(1-oxo-4-carboxybutyl)-N-(3-pyridyl)-indole

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 15.0 of 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole, 100 ml of 0.5N sodium hydroxide is heated under reflux for 16 hours. The solution is acidified to pH of about 6 with hydrochloric and extracted with methylene chloride. The methylene chloride extract is dried over sodium sulfate and evaporated to dryness to give 3-(1-oxo-4-carboxybutyl)-N-(3-pyridyl)-indole, melting point 177°-178°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 16 hours
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. dry with materialis dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bac6c13fde434d098a681ccd1fde0d81
Source dataset
uspto-grants-1986_09
Patent number
US04609733

Reaction notes

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