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

HRID 573793Notes

Reaction equation

[O:1]=[C:2]1[C:6]([C:7]([O:9]CC)=O)=[CH:5][C:4]2([CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[O:3]1.[NH2:17][C:18]1[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20](=[O:26])[CH:19]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(OC(=O)C)C>[OH:9][C:7]1[C:6]2[C:2](=[O:1])[O:3][C:4]3([CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[C:5]=2[C:19]2[C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH2:23][C:18]=2[N:17]=1

Participants

Conditions

Temperature: 200 °C

Procedure

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.

Workup

temperatureThe mixture is cooled to room temperature
customThe product is isolated by filtration
washwashed with ethylacetate

Sources & evidence

ORD record: ord-ccfd95e97fd24f088bf05e0ba45c9dcf
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029544B2

Reaction notes

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