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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 73340Generated: October 29, 2026

Tetrahydrofuran → 6-Methoxy-5-methyl-1H-indole

https://huagongshe.com/reaction/73340

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
Reactant(4-Methoxy-5-methyl-2-nitrophenyl)acetonitrileHCID 58437287—
CatalystHCID 178418390HCID 178418390—
Solvent1-ButanolHCID 263—
Product6-Methoxy-5-methyl-1H-indoleHCID 1980383769.3%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of (4-methoxy-5-methyl-2-nitrophenyl)acetonitrile (0.24 g) in a mixed solvent of tetrahydrofuran (2 mL) and n-butanol (2 mL) was added palladium-carbon powder (0.043 g) under an argon atmosphere and this mixture was stirred at 60° C. under a hydrogen atmosphere for 36 hours. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.13 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829040B2
Source datasetuspto-grants-2014_09
ORD IDord-b2862c0f5dcd4d04acb2d1ace9e19f83
Source noteuspto-grants-2014_09