Ethylene Glycol → 3-(4-Carboxybutyl)-2-(3-pyridyl)indole

HRID 1980868Notes

Reaction equation

HRID 1980868 reaction equation
C(C[CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)#N.[OH-:22].[Na+].[CH2:24]([OH:27])[CH2:25]O>O>[C:24]([CH2:25][CH2:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)([OH:27])=[O:22]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 204007973-(4-Cyanobutyl)-2-(3-pyridyl)indole

Product 1

HCID 204007933-(4-Carboxybutyl)-2-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(4-Cyanobutyl)-2-(3-pyridyl)-indole (540 mg) is heated at 185° for 0.5 hour with 450 mg of powdered NaOH and 5 ml of ethylene glycol; the reaction solution is diluted with 50 ml water, washed with ether, and adjusted to pH 6 with 2N HCl, to give 3-(4-carboxybutyl)-2-(3-pyridyl)indole.

Workup

  1. washwashed with ether

Sources & evidence

ORD record
ord-e18af54c27034d5fb21452734b444fff
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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