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

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%).

1. temperatureThe mixture was heated to 100 degree Celsius
2. temperatureAfter the reaction was refluxed at 120 degree Celsius for 4 h
3. temperaturethe mixture was heated up to 150 degree Celsius
4. customto remove any liquid
5. temperatureFinally, the mixture was heated up to 190 degree Celsius
6. addition300 mL methylene chloride was added
7. filtrationfiltered

ORD record

ord-83e06c847ab448c3baa738badca1f51a

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605265B2