Reaction #83201

Reaction equation

HCl

diethyl carbonate

sodium ethoxide

6H-pyrido[3,2,1-de]acridin-1(2H)-one

→

Ethyl 6H-pyrido[3,2,1-de]acridin-1(2H)-one

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturethe solution was then refluxed for 3 hours
2. 2
   TemperatureThe reaction mixture was cooled
3. 3
   Extractionextracted with methylene chloride
4. 4
   ExtractionThe organic extract
5. 5
   Washwas washed with water
6. 6
   Otherwas then collected
7. 7
   Otherdried
8. 8
   Otherevaporated to dryness
9. 9
   Otherto obtain a light amber solid (1.8 g; m.p. 113°-118° C.)

Procedure

To a freshly prepared solution of sodium ethoxide in ethanol (from 0.35 g sodium metal and 10 ml ethanol) was added 6H-pyrido[3,2,1-de]acridin-1(2H)-one (1.2 g) portionwise over a period of 10 minutes. To the resulting dark red solution was slowly added diethyl carbonate (1.77 g) and the solution was then refluxed for 3 hours. The reaction mixture was cooled, acidified to pH 2 with concentrated HCl and then extracted with methylene chloride. The organic extract was washed with water and was then collected, dried and evaporated to dryness to obtain a light amber solid (1.8 g; m.p. 113°-118° C.).

Source