Formic Acid → n-(3-chlorophenyl)formamide
Reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>>[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH:15][CH:5]=[O:7]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
Acetic anhydride (189 ml, 2.0 mol) was mixed with formic acid (91 ml, 2.4 mol) at 0° C. and the mixture was stirred at 60° C. for 1 h and then cooled to 0° C. To the solution was added dropwise 3-chloroaniline (105.7 ml, 1.0 mol) and the mixture was stirred at room temperature for 18 h. After removal of solvent in vacuo, the residue was extracted with EtOAc-H2O. The organic layer was washed with 5% aqueous citric acid, saturated aqueous NaHCO3 and brine, dried over Na2SO4 and then concentrated. The residue was crystallized from iPr2O to give the title compound (115 g, 0.739 mol, 74%) as a colorless solid.