Ethylene Glycol → Indole

HRID 1263321Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8](O)[CH2:9]O>>[NH:1]1[C:2]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=[CH:8]1

Participants

Reactant 2

HCID 174Ethylene Glycol

HCID 6115Aniline

Product 1

HCID 798IndoleYield 62.3%

Conditions

Temperature: 350 °C

Procedure

93.1 g (1 mole) of aniline and 6.2 g (0.1 mole) of ethylene glycol as well as 3.0 g of the above catalyst were introduced into a stainless steel autoclave having an inner volume of 200 ml. The inside of the autoclave was purged with nitrogen gas and then hydrogen gas was fed to a gauge pressure of 10 kg/cm2. The reaction was conducted under stirring, at 350° C. for one hour. The resulting reaction mixture was analyzed by gas chromatography. Thus, indole was obtained in a yield of 62.3% based on ethylene glycol.

Workup

customThe inside of the autoclave was purged with nitrogen gas
customThe resulting reaction mixture

Sources & evidence

ORD record: ord-2cdc3195a20f4be5830ff0f73d770065
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04456760

Reaction notes

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