Reaction #1121769

Reaction equation

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

NH4Cl

→

4-Hydroxyphenyl 10-methylacridan-9-carboxvlate

Solvents

dichloromethane

ethanol

Conditions

Workup

1. 1
   OtherInto a 50 mL round bottom flask equipped with magnetic stirrer
2. 2
   Temperaturereflux condensor
3. 3
   Temperatureheating mantle under an argon atmosphere
4. 4
   TemperatureThe reaction mixture was refluxed for 2 hrs
5. 5
   Filtrationfiltered
6. 6
   WashThe solid was washed with 2×25 mL of ethanol
7. 7
   ConcentrationThe combined filtrate was concentrated under reduced pressure
8. 8
   Otherto give off-white solid
9. 9
   Washwashed with 100 mL of deionized water
10. 10
    OtherAfter separation the organic layer
11. 11
    Dryingwas dried over anhydrous Na2SO4
12. 12
    Filtrationfiltered
13. 13
    ConcentrationThe solution was concentrated under reduced pressure
14. 14
    Otherpurified by column chromatography on silica gel with 10% ethyl acetate-hexane

Procedure

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-carboxvlate. The structure was confirmed as:

Source