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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1804907Generated: November 2, 2026

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-(Tert-butyl)-6-nitro-1H-indole

https://huagongshe.com/reaction/1804907

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6775—
Reactant2-(tert-Butyl)-6-nitroindolineHCID 57470195—
Solvent1,4-DioxaneHCID 31275—
Product2-(Tert-butyl)-6-nitro-1H-indoleHCID 5747019680.6%

Reaction Steps

To a solution of 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (2.0 g, 9.1 mmol) in 1,4-dioxane (20 mL) was added DDQ at room temperature. After refluxing for 2.5 h, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-1H-indole (1.6 g, 80%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08354427B2
Source datasetuspto-grants-2013_01
ORD IDord-7b462d9982a145219fabcfcf29048590
Source noteuspto-grants-2013_01