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 573793

Reaktionsgleichung

Reaktionsgleichung von HRID 573793
[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

Komponenten

5

Edukt 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 66762200Ethyl 2-oxo-1,8-dioxaspiro[4.5]dec-3-ene-3-carboxylate

Produkt 1

HCID 1784267954-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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. customThe product is isolated by filtration
  3. washwashed with ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-ccfd95e97fd24f088bf05e0ba45c9dcf
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029544B2

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