2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Isopropyl-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 573784

Reaction equation

HRID 573784 reaction equation
[C:1]([C:6]1[C:7](=[O:16])[O:8][C:9]2([CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:10]=1)(=O)[CH:2]([CH3:4])[CH3:3].[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.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>ClCCl.CCOCC.C(OC(=O)C)C>[CH:2]([C:1]1[C:6]2[C:7](=[O:16])[O:8][C:9]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:10]=2[C:19]2[C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH2:23][C:18]=2[N:17]=1)([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 54670067L-Ascorbic AcidHCID 66762855HCID 66762855, compound

Product 1

HCID 667623744-Isopropyl-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

3.12 g 3-Isobutyryl-1,8-dioxaspiro[4.5]dec-3-en-2-one and 2.13 g 3-amino-5,5-dimethylcyclohex-2-enone are mixed and heated to 200° C. for 10 minutes under a vacuo of 20 mbar. The mixture is cooled to room temperature, 15 ml ethylacetate are added and the mixture is stirred for 30 minutes. Then 15 ml petrole ether are added and the precipitate is isolated by filtration. The crude product is dissolved in 350 ml dichloromethane, treated with 2.46 g 2,3dichloro-5,6-dicyano-p-benzoquinone and stirred for 18 hours. 2 g Ascorbic acid are added and the mixture is stirred for 10 minutes. The it is washed for three times with water. The organic phase is dried with sodium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customthe precipitate is isolated by filtration
  3. stirringstirred for 18 hours
  4. stirringthe mixture is stirred for 10 minutes
  5. washThe it is washed for three times with water
  6. dry with materialThe organic phase is dried with sodium sulphate
  7. customthe solvents are evaporated in vacuo
  8. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 50:50)

Sources & evidence

ORD record
ord-c8c75e02cd2941df9fceb65ab2620aad
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Linked notes

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