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Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0 - 20℃; for 4 h; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 0 - 20℃; for 1.5 h;
Diisobutylaluminum hydride (1.0 M in toluene, 28 mL, 28 mmol) was added slowly via syringe to a solution of 3-chloro-4-(trifluoromethyl)benzonitrile (3.79 g, 18.4 mmol) in THF (50 mL) at 0° C. The reaction was allowed to proceed for 2 hr, then warmed to ambient temperature and stirred an additional 2 hr. The reaction was then cooled to 0° C., and quenched with 3 M aq HCl (75 mL). The mixture was allowed to warm to ambient temperature, and stirred vigorously for 1.5 hr. The mixture was then transferred to a separatory funnel and diluted with Et2O. The separated organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (Analogix.(R). Intelliflash 280.(TM).; 15percent EtOAc/hexanes eluant; SF40-150 g column) yielded 2.84 g (74percent) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.21 (s, 1H), 8.12 (d, J=8.1, 1H), 8.07-8.02 (m, 1H).
Diisobutylaluminum hydride (1.0 M in toluene, 28 mL, 28 mmol) was added slowly via syringe to a solution of 3-chloro-4-(trifluoromethyl)benzonitrile (3.79 g, 18.4 mmol) in THF (50 mL) at 0° C. The reaction was allowed to proceed for 2 hr, then warmed to ambient temperature and stirred an additional 2 hr. The reaction was then cooled to 0° C., and quenched with 3 M aq HCl (75 mL). The mixture was allowed to warm to ambient temperature, and stirred vigorously for 1.5 hr. The mixture was then transferred to a separatory funnel and diluted with Et2O. The separated organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (Analogix.(R). Intelliflash 280.(TM).; 15percent EtOAc/hexanes eluant; SF40-150 g column) yielded 2.84 g (74percent) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) delta 10.09 (s, 1H), 8.21 (s, 1H), 8.12 (d, J=8.1, 1H), 8.07-8.02 (m, 1H).
3-chloro-4-(trifluoromethyl)benzamidine hydrochloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A solution of 3-chloro-4-(trifluoromethyl)-benzonitrile (2 g; 98%; 9.53 mmol) in CHCI3 (16 ml) and MeOH (4 ml) was cooled to 0C. Then HCl-gas was bubbled through this solution for 45min. The flask was closed and stored overnight in the fridge. Then argon was bubbled through to remove excess of HCl-gas and all solvents were evaporated. NH3 (2M solution in MeOH; 24 ml; 47.7 mmol) was added and the solution was stirred at RT for 2 h. The reaction mixture was concentrated to dryness. Then again NH3 (2M solution MeOH; 24 ml; 47.7 mmol) was added and the reaction mixture was stirred at RT overnight. The solvents were removed and the remaining white foamy solid (2.56 g) was used without purification for the next step. MS (ESI): 223.1 (M+H)+.
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