Hydrochloric Acid → 5-[1-(Pyridin-3-yl)-1H-indol-3-yl]pentanoic acid

HRID 64681Notes

Reaction equation

HRID 64681 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:11]=1)=[O:5])C.[OH-].[Na+].Cl>>[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:11]=1)([OH:5])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 134903513-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole

Product 1

HCID 134903525-[1-(Pyridin-3-yl)-1H-indol-3-yl]pentanoic acid

Procedure

A suspension of 0.46 g of 3-(4-ethoxycarbonylbutyl)-N-(3-pyridyl)-indole in 85 ml of aqueous 1N sodium hydroxide solution is heated at 95° for 8 hours. The resulting solution is neutralized with hydrochloric acid to pH of about 5.5. The resulting precipitate is filtered off, and triturated with acetonitrile to yield 3-(4-carboxybutyl)-N-(3-pyridyl)-indole (European Patent Application No. 126,401). 3-(4-Carboxybutyl)-N-(3-pyridyl)-indole has melting point of 122°-124°.

Workup

  1. temperatureis heated at 95° for 8 hours
  2. filtrationThe resulting precipitate is filtered off
  3. customtriturated with acetonitrile

Sources & evidence

ORD record
ord-ad9fe2baccd64a3ea0e60ffd82f135e6
Source dataset
uspto-grants-1986_09
Patent number
US04609733

Reaction notes

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