Ethylene Glycol → 1-Methylindole

HRID 623241Notes

Reaction equation

HRID 623241 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9](O)[CH2:10]O>[Ru]>[CH3:1][N:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 7515N-Methylaniline

Product 1

HCID 117811-MethylindoleYield 51%

Reagents, catalysts & solvents 1

HCID 23950RutheniumCatalyst

Procedure

In Tetrahedron Letters, Vol. 27, No. 3, pp. 377-380, 1986, Watanabe discloses the reaction of N-methylaniline with ethylene glycol in the presence of a homogeneous ruthenium catalyst to provide a 51% yield of 1-methylindole. He also reported that: ##STR4##

Sources & evidence

ORD record
ord-50c3f3df2a0e417fb594119b9c8f892a
Source dataset
uspto-grants-1988_09
Patent number
US04774336

Reaction notes

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