O-Toluidine → N-(2-methylphenyl)butanamide
Reaction equation
[C:1]([NH:6][C:7]1[CH:16]=[CH:15][C:10](C(OC)=O)=[CH:9][C:8]=1[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4].NC1C(C)=CC=CC=1.C(Cl)(=O)CCC>>[C:1]([NH:6][C:7]1[CH:16]=[CH:15][CH:10]=[CH:9][C:8]=1[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]Participants
4
Procedure
A process for preparing methyl N-butyryl-4-amino-3-methyl-benzoate, comprising a first step of reacting o-toluidine with butyryl chloride to give N-butyryl-2-methylaniline, a second step of brominating the N-butyryl-2-methylaniline to give N-(4-bromo-2-methylphenyl)butanamide and a third step of converting the N-(4-bromo-2-methylphenyl)butanamide by reaction with carbon monoxide and methanol in the presence of a palladium catalyst to give methyl N-butyryl-4-amino-3-methylbenzoate.