تفاعل #155393

معادلة التفاعل

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

NH4Cl

→

4-Hydroxyphenyl 10-methylacridan-9-carboxylate

المذيبات

dichloromethane

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىInto a 50 mL round bottom flask equipped with magnetic stirrer
2. 2
   درجة الحرارةreflux condensor
3. 3
   درجة الحرارةheating mantle under an argon atmosphere
4. 4
   درجة الحرارةThe reaction mixture was refluxed for 2 hrs
5. 5
   ترشيحfiltered
6. 6
   غسيلThe solid was washed with 2×25 mL of ethanol
7. 7
   تركيزThe combined filtrate was concentrated under reduced pressure
8. 8
   أخرىto give off-white solid
9. 9
   غسيلwashed with 100 mL of deionized water
10. 10
    أخرىAfter separation the organic layer
11. 11
    تجفيفwas dried over anhydrous Na2SO4
12. 12
    ترشيحfiltered
13. 13
    تركيزThe solution was concentrated under reduced pressure
14. 14
    أخرىpurified by column chromatography on silica gel with 10% ethyl acetate-hexane

الإجراء التجريبي

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:

المصدر