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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 573793Generated: October 25, 2026

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Hydroxy-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

https://huagongshe.com/reaction/573793

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6775—
Reactant3-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 136680—
ReactantEthyl 2-oxo-1,8-dioxaspiro[4.5]dec-3-ene-3-carboxylateHCID 66762200—
SolventEthyl AcetateHCID 8857—
Product4-Hydroxy-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dioneHCID 178426795—

Reaction Conditions

Temperature200 °C

Reaction Steps

10 g Ethyl 2-oxo-1,8-dioxaspiro[4.5]dec-3-ene-3-carboxylate and 6.15 g 3-amino-5,5-dimethylcyclohex-2-enone are mixed and heated to 200° C. for 20 minutes under a vacuo of 20 mbar. The mixture is cooled to room temperature and dissolved in 100 ml ethylacetate. 10 g 2,3-dichloro-5,6-dicyano-p-benzoquinone are added and the mixture is stirred for 4 hours at 50° C. and for 18 hours at room temperature. The product is isolated by filtration and washed with ethylacetate.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09029544B2
Source datasetuspto-grants-2015_05
ORD IDord-ccfd95e97fd24f088bf05e0ba45c9dcf
Source noteuspto-grants-2015_05