Reaction #155312

Reaction equation

2,2-Dimethyl-5-[(3-propoxynaphthalen-2-ylamino) methylene][1,3]dioxane-4,6-dione

diphenyl ether

→

5-propoxy-4H-benzo[f]quinolin-1-one

Yield 106.3%

Conditions

Workup

1. 1
   Temperaturethe mixture was heated with a mantle heater
2. 2
   Temperaturemaintained
3. 3
   Temperatureunder reflux for 2 hours
4. 4
   Otherpurified
5. 5
   ConcentrationThe purified product was concentrated to dryness under reduced pressure

Procedure

2,2-Dimethyl-5-[(3-propoxynaphthalen-2-ylamino) methylene][1,3]dioxane-4,6-dione (4.19 g, 11.7 mmol) was added to diphenyl ether (15 ml), and the mixture was heated with a mantle heater and then maintained under reflux for 2 hours. The mixture was cooled to room temperature and purified using silica gel column chromatography (dichloromethane:methanol=70:1→9:1). The purified product was concentrated to dryness under reduced pressure, giving a dark brown powder of 5-propoxy-4H-benzo[f]quinolin-1-one (3.15 g, yield: 61%).

Source