Water → HCID 14071976, compound

HRID 2352557Notes

Reaction equation

HRID 2352557 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[K+].Cl[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1.O>CS(C)=O>[N:15]1[CH:16]=[CH:17][N:18]=[CH:19][C:14]=1[O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 73277ChloropyrazineHCID 754211H-indol-4-ol

Product 1

HCID 14071976HCID 14071976, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2.66 g of 4-hydroxyindole in 60 ml of DMSO is combined with 1.4 g of potassium hydroxide (pulverized) and stirred under an N2 atmosphere for one hour at room temperature. After adding 2.5 g of 2-chloropyrazine, the mixture is heated for 2 hours to 100° C., poured into water, and extracted with ethyl acetate. The residue from the organic phase is purified over silica gel, thus obtaining 2.95 g (70%) of 4-(2-pyrazinyloxy)indole, mp 192°-193° C.

Workup

  1. temperaturethe mixture is heated for 2 hours to 100° C.
  2. extractionextracted with ethyl acetate
  3. customThe residue from the organic phase is purified over silica gel

Sources & evidence

ORD record
ord-b7835c5e357241aaa2d27bf284b69719
Source dataset
uspto-grants-1989_10
Patent number
US04877792

Reaction notes

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