Reacción #93973

Ecuación de reacción

ethyl bromoacetate

7-Hydroxy-5,6-dihydro-4H-dibenzo[de,h]quinoline

sodium hydride

→

Ethyl (5,6-dihydro-4H-dibenzo[de,h]quinol-7-yloxy)acetate

Rendimiento 46.0%

Disolventes

dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONis distilled water (10 cc)
2. 2
   workup.ADDITIONis added
3. 3
   Concentraciónthe mixture is concentrated to a volume of 400 cc
4. 4
   workup.DISTILLATIONdistilled water (4600 cc)
5. 5
   workup.ADDITIONis added
6. 6
   Extracciónthe mixture is extracted eight times with diethyl ether (total 3500 cc)
7. 7
   LavadoThe combined organic solutions are washed four times with distilled water (total 4000 cc)
8. 8
   Secadodried over anhydrous sodium sulphate
9. 9
   workup.ADDITIONtreated with decolourising charcoal (5 g)
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporated to dryness
12. 12
    SecadoThe residue is dried by azeotropic distillation with methylene chloride (150 cc)
13. 13
    Otrocrystallised from ethanol (16 cc)
14. 14
    TemperaturaAfter cooling for 21 hours at about 5° C.
15. 15
    Filtraciónthe resulting crystals are filtered off
16. 16
    Lavadowashed twice with ethanol (total 18 cc), which
17. 17
    Temperaturahas been cooled to -20° C.
18. 18
    Otrodried under reduced pressure (20 mm Hg) at 20° C

Procedimiento

7-Hydroxy-5,6-dihydro-4H-dibenzo[de,h]quinoline (27 g) [prepared as described in Example 2] is added to a suspension of sodium hydride (50% dispersion in mineral oil; (5.75 g) in anhydrous dimethylformamide (520 cc) and then, after stirring for 4 hours, ethyl bromoacetate (21.3 g) in solution in anhydrous dimethylformamide (20 cc) is added. The reaction mixture is maintained for 22 and a half hours at about 20° C., is distilled water (10 cc) is added, the mixture is concentrated to a volume of 400 cc, distilled water (4600 cc) is added and the mixture is extracted eight times with diethyl ether (total 3500 cc). The combined organic solutions are washed four times with distilled water (total 4000 cc), dried over anhydrous sodium sulphate, treated with decolourising charcoal (5 g), filtered and evaporated to dryness. The residue is dried by azeotropic distillation with methylene chloride (150 cc) and then crystallised from ethanol (16 cc). After cooling for 21 hours at about 5° C., the resulting crystals are filtered off, washed twice with ethanol (total 18 cc), which has been cooled to -20° C., and dried under reduced pressure (20 mm Hg) at 20° C. Ethyl (5,6-dihydro-4H-dibenzo[de,h]quinol-7-yloxy)acetate (16.95 g), melting at 70° C., is thus obtained.

Fuente