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ChemicalBook CAS DataBase List 4,6,7,8-TETRAHYDRO-1H,3H-QUINOLINE-2,5-DIONE
5057-12-5

4,6,7,8-TETRAHYDRO-1H,3H-QUINOLINE-2,5-DIONE synthesis

3synthesis methods
-

Yield: 92%

Reaction Conditions:

with ammonium acetate at 80; for 5 h;Inert atmosphere;Michael Addition;Temperature;Time;Reagent/catalyst;

Steps:

General Procedure for Synthesis of 3,4,7,8-Tetrahydroquinoline-2,5(1H,6H)-dione (4a)
General procedure: 1,3-Dicarbonyls (8.9 mmol, 1 equiv.) followed by ammonium acetate (10.6 mmol, 1.2 mmol, 1.2 equiv.) were added to the solution of acrylic acid (10.6 mmol, 1.2 equiv.). The reactant mass was mixed thoroughly with a spatula and heated at 80 °C with stirring under a nitrogen atmosphere for 5 h. After cooling, the reaction mixture was diluted with 10mL distilled water and extracted twice with ethyl acetate (210 mL). The organic extracts were dried over anhydrous Na2SO4. After filtration, the solvent was evaporated under reduced pressure and subjected to column chromatography (ethyl acetate=hexane) to obtain pure products. The characterization data of the compounds are given.

References:

Senthil Kumar;Kumari, Neeta;Luthra, Pratibha Mehta [Synthetic Communications,2013,vol. 43,# 22,p. 3010 - 3019] Location in patent:supporting information