Reacción #155393

Ecuación de reacción

4-(tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate

NH4Cl

→

4-Hydroxyphenyl 10-methylacridan-9-carboxylate

Disolventes

dichloromethane

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroInto a 50 mL round bottom flask equipped with magnetic stirrer
2. 2
   Temperaturareflux condensor
3. 3
   Temperaturaheating mantle under an argon atmosphere
4. 4
   TemperaturaThe reaction mixture was refluxed for 2 hrs
5. 5
   Filtraciónfiltered
6. 6
   LavadoThe solid was washed with 2×25 mL of ethanol
7. 7
   ConcentraciónThe combined filtrate was concentrated under reduced pressure
8. 8
   Otroto give off-white solid
9. 9
   Lavadowashed with 100 mL of deionized water
10. 10
    OtroAfter separation the organic layer
11. 11
    Secadowas dried over anhydrous Na2SO4
12. 12
    Filtraciónfiltered
13. 13
    ConcentraciónThe solution was concentrated under reduced pressure
14. 14
    Otropurified by column chromatography on silica gel with 10% ethyl acetate-hexane

Procedimiento

Into a 50 mL round bottom flask equipped with magnetic stirrer, reflux condensor and heating mantle under an argon atmosphere was charged a solution of 1.42 parts of the 4-(tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate in 200 mL of ethanol. Then 16 arts NH4Cl was added in five portions, followed by 19.3 parts of Zn in five portions to a hot yellow solutions causing immediate decolorization of the solution. The reaction mixture was refluxed for 2 hrs and filtered. The solid was washed with 2×25 mL of ethanol. The combined filtrate was concentrated under reduced pressure to give off-white solid. The solid was dissolved in 250 mL of dichloromethane and washed with 100 mL of deionized water. After separation the organic layer was dried over anhydrous Na2SO4 and filtered. The solution was concentrated under reduced pressure and purified by column chromatography on silica gel with 10% ethyl acetate-hexane to yield 0.76 parts of 4-Hydroxyphenyl 10-methylacridan-9-carboxylate. The structure was confirmed as:

Fuente