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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 400460Generated: October 30, 2026

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Methyl-3-oxo-2,3,5,6,8,9-hexahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/400460

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6775—
ReactantPotassium CarbonateHCID 11430—
Reactant2-Methyl-3-oxo-2,3,4,4a,5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl esterHCID 86686058—
Solvent1,4-DioxaneHCID 31275—
Product2-Methyl-3-oxo-2,3,5,6,8,9-hexahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl esterHCID 8668605952.4%

Reaction Steps

3 g DDQ was added to 2.5 g 2-methyl-3-oxo-2,3,4,4a,5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester in 25 mL dioxane. The reaction was refluxed for 12 h. Then aqueous potassium carbonate solution was added and the mixture was extracted with chloroform. The organic layer was washed with brine. The crude product was purified by column chromatography on silica gel to yield 1.3 g of the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08741892B2
Source datasetuspto-grants-2014_06
ORD IDord-3d7c3baae2f74170bb803737c9f5c040
Source noteuspto-grants-2014_06