2-(4-Chlorophenoxy)benzonitrile → (2-(4-chlorophenoxy)phenyl)MethanaMine

Participants

Reaction Steps

AMR01073 To an ice cooled solution of 2-(4-chlorophenoxy)benzonitrile (AMR01071, 200 mg, 8.75 mmol) in dry THF (10 mL) was added a solution of LiAlH4 (THF 1M, 1.75 mL) under nitrogen. After stirring at room temperature for 3 h, the reaction mixture was cooled again and quenched with the minimum amount of saturated NH4Cl solution. The insoluble material was removed by filtration, and washed with DCM. The filtrate was dried (MgSO4) and the solvent evaporated to give 2-(4-chlorophenoxy)benzylamine (AMR01073, 203 mg, 100%) as an oil, which was used in the next step without further purification. AMR01076 Following the same procedure, from AMR01071 (1.5 g, 6.53 mmol) and LiAlH4 solution (THF 1M, 13 mL) in dry THF (30 mL), 2-(4-chlorophenoxy)benzylamine (AMR0106, 1.38 g, 90%) was obtained as an oil. Rf: 0.35 (DCM/MeOH 9:1) 1H NMR (270 MHz, CDCl3) δ 1.42 (2H, br s, NH2), 3.84 (2H, s, CH2), 6.84-6.90 (3H, m, ArH), 7.13 (1H, m, ArH), 7.21 (1H, dd, J=7.6, 2.0 Hz, ArH), 7.26 (2H, AA′BB′, ArH) and 7.38 (1H, td, J=7.4, 1.7 Hz, ArH). LC/MS (APCI) tr=1.40 min, m/z 236.38 (34), 234.36 (M++H, 100), 217.29 (M+—NH3, 35).

Provenance & Evidence