4-(Phenylamino)benzoic acid → Methyl 4-anilinobenzoate
Reaction equation
[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:18]O>>[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([O:14][CH3:18])=[O:13])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
3
Procedure
30 ml of 10% hydrogen chloride-methanol was added to 1.59 g (7.46 mmol) of 4-(phenylamino)benzoic acid and the mixture was refluxed overnight under heating. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed with a sodium hydrogencarbonate aqueous solution and brine, and dried (MgSO4). The solvent was distilled off and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1 (v/v)) to obtain 1.66 g (7.30 mmol) of methyl 4-(phenylamino)benzoate as a pale yellow solid. Its spectroscopic data are as follows:
Workup
- temperaturethe mixture was refluxed overnight
- temperatureunder heating
- concentrationAfter the reaction mixture was concentrated under reduced pressure