3-Aminocyclohex-2-en-1-one → 2-Hydroxy-7,8-dihydro-5(6H)-quinolinone

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Reaction Steps

To a 500 mL flask, added 3-amino-cyclohex-2-enone (110 g, 0.99 moL) and ethyl propiolate (100 mL, 0.99 moL) and attached a condenser. The mixture was heated to 100 degree Celsius. The reaction started slowly at beginning and accelerated as the reaction progress. After the reaction was refluxed at 120 degree Celsius for 4 h, the mixture was heated up to 150 degree Celsius to remove any liquid. Finally, the mixture was heated up to 190 degree Celsius and remained for 1 h. The reaction was cooled to room temperature and 300 mL methylene chloride was added. The mixture was trituated and filtered to give the desired product (34 g, 21%).

Provenance & Evidence