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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 73920Generated: October 25, 2026

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

https://huagongshe.com/reaction/73920

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 numberUS08829204B2
Source datasetuspto-grants-2014_09
ORD IDord-f978194ce5ef4948baf31dac0edec27c
Source noteuspto-grants-2014_09