2-amino-2-(3-bromophenyl)propanenitrile

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). The mixture was extracted with diethylether (3×300 ml) The organic phase was washed with water and brine dried with Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). 1H-NMR (400 MHz, CDCl3): 7.84 (s, 1H), 7.59 (d, 1H), 7.48 (d, 1H), 7.28 (m, 1H), 1.75 (s, 3H). The mixture was extracted with diethylether (3×300 ml) The organic phase was washed with water and brine dried with Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). 1H-NMR (400 MHz, CDCl3): 7.84 (s, 1H), 7.59 (d, 1H), 7.48 (d, 1H), 7.28 (m, 1H), 1.75 (s, 3H). The mixture was extracted with diethylether (3×300 ml) The organic phase was washed with water and brine dried with Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). 1H-NMR (400 MHz, CDCl3): 7.84 (s, 1H), 7.59 (d, 1H), 7.48 (d, 1H), 7.28 (m, 1H), 1.75 (s, 3H). The mixture was extracted with diethylether (3×300 ml) The organic phase was washed with water and brine dried with Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: rac-2-Amino-2-(3-bromo-phenyl)-propionitrile (20 g, 88.9 mmol) was dissolved in HCl/MeOH (500 mL) and the mixture was refluxed for 4 days. After cooling to room temperature, AcOEt (100 mL) and water (100 mL) were added and the mixture was extracted with AcOEt (2×100 mL). The combined aqueous layers were basified with aqueous ammonia solution until pH 8 and extracted with AcOEt (5×100 mL). The combined organic layers were dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield rac-2-amino-2-(3-bromo-phenyl)-propionic acid methyl ester (10.6 g, 46% yield) as an oil. the mixture was refluxed for 4 days the mixture was extracted with AcOEt (2×100 mL) extracted with AcOEt (5×100 mL) The combined organic layers were dried (Na2SO4) filtered the solvents evaporated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Trimethylsilylcyanide (20 g, 200 mmol) was added to a stirred solution of 3-bromoacetophenone (20 g, 100 mmol) and NH4Cl (11 g, 200 mmol) in NH3/MeOH (400 mL). The mixture was stirred at room temperature for 4 days. Then the solvent was evaporated in vacuo and the residue was taken up in AcOEt (100 mL). The solid was filtered off and the filtrate was evaporated in vacuo to yield rac-2-amino-2-(3-bromo-phenyl)-propionitrile (20 g, 86% yield) which was used in the next step without further purification. Then the solvent was evaporated in vacuo The solid was filtered off the filtrate was evaporated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). 11H-NMR (400 MHz, CDCl3): 7.84 (s, 1H), 7.59 (d, 1H), 7.48 (d, 1H), 7.28 (m, 1H), 1.75 (s, 3H). The mixture was extracted with diethylether (3×300 ml) The organic phase was washed with water and brine dried with Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). The mixture was extracted with diethylether (3×300 ml) The organic phase was washed with water and brine dried with Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). 1H-NMR (400 MHz, CDCl3): 7.84 (s, 1H), 7.59 (d, 1H), 7.48 (d, 1H), 7.28 (m, 1H), 1.75 (s, 3H). The mixture was extracted with diethylether (3×300 ml) The organic phase was washed with water and brine dried with Na2SO4 concentrated in vacuo