4-(Trifluoromethoxy)benzonitrile → 4-(Trifluoromethoxy)benzamidoxime
Reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[NH2:14][OH:15].Cl>CCO>[OH:15][NH:14][C:8](=[NH:9])[C:7]1[CH:10]=[CH:11][C:4]([O:3][C:2]([F:1])([F:12])[F:13])=[CH:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(trifluoromethoxy)benzonitrile (2.0 g, 10.6 mmol) in EtOH (20 mL), TEA (53 g, 53.0 mmol) and NH2OH.HCl (3.6 g, 26.5 mmol) were added in sequence. The mixture was refluxed for 4 h, cooled to RT, and concentrated under reduced pressure. The residue was diluted with H2O (20 mL), and extracted with EtOAc (20 mL×3). The combined organic layers were washed with H2O (1×10 mL) and brine (1×10 mL), dried over Na2SO4, filtered and concentrated to afford the crude N-hydroxy-4-(trifluoromethoxy)benzimidamide (2.0 g, 85%), which was directly used for next reaction without further purification. MS (ES+) C8H7F3N2O2 requires: 220, found: 221 [M+H]+.