2-(4-aminophenyl)propanenitrile

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A solution of 2-(4-Amino-phenyl)-propionitrile (10.2 g, 69.8 mmol) in pyridine (40 mL) was added Ac2O (7.49 g, 73.4 mmol) at room temperature. The reaction mixture was refluxed for 1 hrs then cooled to room temperature, and concentrated in vacuo. The reaction mixture was refluxed for 1 hrs concentrated in vacuo

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

実験手順: A solution of 2-(4-Amino-phenyl)-propionitrile (10.2 g, 69.8 mmol) in pyridine (40 mL) was added Ac2O (7.49 g, 73.4 mmol) at room temperature. The reaction mixture was refluxed for 1 hrs then cooled to room temperature, and concentrated in vacuo. The reaction mixture was refluxed for 1 hrs concentrated in vacuo

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

実験手順: To the flask was added THF/EtOH (1:1, 70 mL) followed by 2-(4-nitrophenyl)-propionitrile (13.2 g, 74.9 mmol) and 10% palladium carbon (1.07 g) at room temperature. The reaction mixture was hydrogenated and stirred for 30 minutes at 47 psi to 28 psi then filtered through celite bed, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:3) as eluant. then filtered through celite bed washed with EtOAc The filtrate was concentrated in vacuo The residue was purified by flash column chromatography on silica gel

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

実験手順: A solution of 2-(4-Amino-phenyl)-propionitrile (10.2 g, 69.8 mmol) in pyridine (40 mL) was added Ac2O (7.49 g, 73.4 mmol) at room temperature. The reaction mixture was refluxed for 1 hrs then cooled to room temperature, and concentrated in vacuo. The reaction mixture was refluxed for 1 hrs concentrated in vacuo

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

実験手順: A solution of 2-(4-Amino-phenyl)-propionitrile (10.2 g, 69.8 mmol) in pyridine (40 mL) was added Ac2O (7.49 g, 73.4 mmol) at room temperature. The reaction mixture was refluxed for 1 hrs then cooled to room temperature, and concentrated in vacuo. The reaction mixture was refluxed for 1 hrs concentrated in vacuo

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

実験手順: To the flask was added THF/EtOH (1:1, 70 mL) followed by 2-(4-nitrophenyl)-propionitrile (13.2 g, 74.9 mmol) and 10% palladium carbon (1.07 g) at room temperature. The reaction mixture was hydrogenated and stirred for 30 minutes at 47 psi to 28 psi then filtered through celite bed, and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:3) as eluant. then filtered through celite bed washed with EtOAc The filtrate was concentrated in vacuo The residue was purified by flash column chromatography on silica gel

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 27.4 g of bromine in 87.5 ml of 95% v/v acetic acid were added dropwise to a stirred mixture of 25 g of 2-(p-aminophenyl)propionitrile [British Pat. No. 1,198,212], 66.8 g of potassium thiocyanate and 300 ml of 95% v/v acetic acid at ambient temperature. The mixture was then stirred at 50° C. for a further 2 hours before being poured into 1.5 liters of water. The solution obtained was filtered through celite and sodium bicarbonate was then added to the filtrate until no further precipitation occurred. The precipitate was collected and crystallized from methanol/water to give 19.4 g (56%) of 2-amino-α-methyl benzothiazole-6-acetonitrile as yellow prisms melting at 165.1° C. at ambient temperature The solution obtained was filtered through celite and sodium bicarbonate was then added to the filtrate until no further precipitation The precipitate was collected crystallized from methanol/water

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 27.4 g of bromine in 87.5 ml of 95% v/v acetic acid were added dropwise to a stirred mixture of 25 g of 2-(p-aminophenyl)propionitrile [British Pat. No. 1,198,212], 66.8 g of potassium thiocyanate and 300 ml of 95% v/v acetic acid at ambient temperature. The mixture was then stirred at 50° C. for a further 2 hours before being poured into 1.5 liters of water. The solution obtained was filtered through celite and sodium bicarbonate was then added to the filtrate until no further precipitation occurred. The precipitate was collected and crystallized from methanol/water to give 19.4 g (56%) of 2-amino-α-methyl benzothiazole-6-acetonitrile as yellow prisms melting at 165.1° C. at ambient temperature The solution obtained was filtered through celite and sodium bicarbonate was then added to the filtrate until no further precipitation The precipitate was collected crystallized from methanol/water

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

実験手順: Finely ground 2-(4-aminophenyl) propionitrile (73 g., 0.5 mole) was suspended in concentrated hydrochloric acid (125 ml.). The stirred suspension was diazotised at 0°-5° C. by the dropwise addition of a solution of sodium nitrite (36.23 g., 0.525 mole) in water (60 ml.) during 1- 2 hours. The almost clear solution was stirred for a further 20 minutes at 5°-10° C., then poured into a stirred, boiling solution of concentrated sulphuric acid (250 ml.) in water (2.5 l.). After 6 minutes it was cooled in an ice-bath, then extracted with ether (×4). The combined ether extracts were extracted with 2N-sodium hydroxide (×6). The combined alkaline extracts were cooled in ice-bath, acidified with concentrated hydrochloric acid and extracted with ether (×3). The combined ether extracts were washed with saturated sodium chloride solution (×3), dried (Na2SO4) and evaporated to leave a dark brown oil (66.7 g.) which on distillation gave 2-(4-hydroxyphenyl) propionitrile (59.58 g.), b.p. 112°-122° C./0.125 m.m., m.p. 41°-46° C. poured into a stirred After 6 minutes it was cooled in an ice-bath extracted with ether (×4) The combined ether extracts were extracted with 2N-sodium hydroxide (×6) The combined alkaline extracts were cooled in ice-bath extracted with ether (×3) The combined ether extracts were washed with saturated sodium chloride solution (×3) dried (Na2SO4) evaporated to leave a dark brown oil (66.7 g.) which on distillation

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

実験手順: Finely ground 2-(4-aminophenyl) propionitrile (73 g., 0.5 mole) was suspended in concentrated hydrochloric acid (125 ml.). The stirred suspension was diazotised at 0°-5° C. by the dropwise addition of a solution of sodium nitrite (36.23 g., 0.525 mole) in water (60 ml.) during 1- 2 hours. The almost clear solution was stirred for a further 20 minutes at 5°-10° C., then poured into a stirred, boiling solution of concentrated sulphuric acid (250 ml.) in water (2.5 l.). After 6 minutes it was cooled in an ice-bath, then extracted with ether (×4). The combined ether extracts were extracted with 2N-sodium hydroxide (×6). The combined alkaline extracts were cooled in ice-bath, acidified with concentrated hydrochloric acid and extracted with ether (×3). The combined ether extracts were washed with saturated sodium chloride solution (×3), dried (Na2SO4) and evaporated to leave a dark brown oil (66.7 g.) which on distillation gave 2-(4-hydroxyphenyl) propionitrile (59.58 g.), b.p. 112°-122° C./0.125 m.m., m.p. 41°-46° C. poured into a stirred After 6 minutes it was cooled in an ice-bath extracted with ether (×4) The combined ether extracts were extracted with 2N-sodium hydroxide (×6) The combined alkaline extracts were cooled in ice-bath extracted with ether (×3) The combined ether extracts were washed with saturated sodium chloride solution (×3) dried (Na2SO4) evaporated to leave a dark brown oil (66.7 g.) which on distillation