反应详情

4-fluorophenyhydrazine (0.90 g, 7.14 mmol) was dissolved in glacial acetic acid (25 mL) under a nitrogen atmosphere and added dropwise to a refluxing solution of 3-cyclohexanonecarboxylic acid ethyl ester (1.73 g, 10 mmol) dissolved in glacial acetic acid (15 mL). After the addition was complete, the solution was heated under reflux for 1 hr, cooled to room temperature and allowed to stir overnight. The orange solution was evaporated under reduced pressure to give a yellow-brown solid. The solid was suspended in 10% sulfuric acid and heated under reflux for 5 hrs, cooled to room temperature and allowed to stir overnight. The brown solid was collected by filtration and recrystallized from acetic acid and water to give the compound I (1.21 g), mp: >200° C. MS [M−H]− m/z 232.

1. additionAfter the addition
2. temperaturethe solution was heated
3. temperatureunder reflux for 1 hr
4. customThe orange solution was evaporated under reduced pressure
5. customto give a yellow-brown solid
6. temperatureheated
7. temperatureunder reflux for 5 hrs
8. temperaturecooled to room temperature
9. stirringto stir overnight
10. filtrationThe brown solid was collected by filtration
11. customrecrystallized from acetic acid and water