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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2189537Generated: October 30, 2026

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

https://huagongshe.com/reaction/2189537

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 numberUS08324242B2
Source datasetuspto-grants-2012_12
ORD IDord-d6e0ad906b6d4899af99d6c65a7055bf
Source noteuspto-grants-2012_12