Ammonium Chloride → 4-Hydroxyphenyl 10-methylacridan-9-carboxvlate

HRID 68211Notes

Reaction equation

HRID 68211 reaction equation
FC(F)(F)S([O-])(=O)=O.[CH3:9][N+:10]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][Si](C(C)(C)C)(C)C)=[CH:29][CH:28]=2)=[O:25])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2.[NH4+].[Cl-]>C(O)C.ClCCl.[Zn]>[CH3:9][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]([C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[O:25])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]1=2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 866153714-(Tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate

Product 1

HCID 544188774-Hydroxyphenyl 10-methylacridan-9-carboxvlate

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

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-carboxylate. The structure was confirmed as:

Workup

  1. customInto a 50 mL round bottom flask equipped with magnetic stirrer
  2. temperaturereflux condensor
  3. temperatureheating mantle under an argon atmosphere
  4. temperatureThe reaction mixture was refluxed for 2 hrs
  5. filtrationfiltered
  6. washThe solid was washed with 2×25 mL of ethanol
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. customto give off-white solid
  9. washwashed with 100 mL of deionized water
  10. customAfter separation the organic layer
  11. dry with materialwas dried over anhydrous Na2SO4
  12. filtrationfiltered
  13. concentrationThe solution was concentrated under reduced pressure
  14. custompurified by column chromatography on silica gel with 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-883438eaf170468d9b832713eadcafcc
Source dataset
uspto-grants-2014_09
Patent number
US08822233B2

Reaction notes

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