Trifluoroacetic acid → 2-(Benzamido)-4-(4-(dimethylamino)phenyl)benzoic acid
Reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([N:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21]C(C)(C)C)=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:8]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][C:33]([N:36]([CH3:38])[CH3:37])=[CH:34][CH:35]=2)[CH:27]=[CH:26][C:18]=1[C:19]([OH:21])=[O:20])(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1Participants
3
Procedure
5.0 mL of trifluoroacetic acid was added to the obtained tert-butyl 2-(benzamido)-4-(4-(dimethylamino)phenyl)benzoate and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, ethyl acetate and water were added and pH was adjusted to pH 6.5 with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. Methanol was added to the obtained residue and a solid substance was separated by filtration to obtain 3.8 mg of 2-(benzamido)-4-(4-(dimethylamino)phenyl)benzoic acid as pale yellow solid.