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

HRID 1700510Notes

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][C:18]=3[Cl:23])[CH2:14][C:13](=[O:24])[CH:12]=2)C(=O)O1>C1(OC2C=CC=CC=2)C=CC=CC=1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:15]1[CH2:16][C:11]2[NH:10][CH:9]=[CH:5][C:6](=[O:8])[C:12]=2[C:13](=[O:24])[CH2:14]1

Participants

Conditions

Temperature: 260 °C

Procedure

A mixture of 2,2-dimethyl-5-[(3-oxo-5-(2-chlorophenyl)-1-cyclohexenylamino)methylene]-[1,3]dioxane-4,6-dione (1.6 g) in diphenylether (20 ml) was stirred at 260° C. for 30 minutes. Under reduced pressure, the solvent was evaporated, and the resulting crystals were washed with petroleum ether and recrystallized from ethanol to give 7-(2-chlorophenyl)-1,4,5,6,7,8-hexahydroquinoline-4,5-dione (1.1 g).

Workup

customUnder reduced pressure, the solvent was evaporated
washthe resulting crystals were washed with petroleum ether
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-68e58cc5bded4ba697f018c098321450
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350749B1

Reaction notes

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