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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1727489Generated: October 31, 2026

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

https://huagongshe.com/reaction/1727489

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 numberUS07495103B2
Source datasetuspto-grants-2009_02
ORD IDord-33f5d1cb4e5149c2ac1e315124dabecf
Source noteuspto-grants-2009_02