2,2-Dimethyl-5-[(3-oxo-5-phenyl-1-cyclohexenylamino)methylene]-[1,3]dioxane-4,6-dione → 7-Phenyl-1,4,5,6,7,8-hexahydroquinoline-4,5-dione

HRID 1700505Notes

Reaction equation

HRID 1700505 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][C:13](=[O:23])[CH:12]=2)C(=O)O1>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:17]1([CH:15]2[CH2:16][C:11]3[NH:10][CH:9]=[CH:5][C:6](=[O:8])[C:12]=3[C:13](=[O:23])[CH2:14]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 183175972,2-Dimethyl-5-[(3-oxo-5-phenyl-1-cyclohexenylamino)methylene]-[1,3]dioxane-4,6-dione

Product 1

HCID 183177747-Phenyl-1,4,5,6,7,8-hexahydroquinoline-4,5-dioneYield 72.8%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 2,2-dimethyl-5-[(3-oxo-5-phenyl-1-cyclohexenylamino)methylene]-[1,3]dioxane-4,6-dione (1.0 g) in diphenylether (15 ml) was stirred at 260-280° C. for 30 minutes. Under reduced pressure, the solvent was evaporated, and the resulting crystals were washed with petroleum ether. The crystals were recrystallized from ethanol to give crystals of 7-phenyl-1,4,5,6,7,8-hexahydroquinoline-4,5-dione (0.51 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. washthe resulting crystals were washed with petroleum ether
  3. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-cef436510e1b4e6eadb1c68cb25939c5
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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