4-(烯丙氧基)苯胺

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-acetoxy-2-bromoquinolizinium bromide (10.0 g., 0.029 mole) in isopropanol (200 ml.) was added p-allyloxyaniline (11.0 g., 0.068 mole). The stirred mixture was boiled under reflux for 4.5 hours. The reaction mixture was cooled at room temperature overnight, and the solid was removed by filtration and washed with ether, providing 5.0 g. of product. The supernatant solution was treated with ether and refrigerated, providing another 5.0 g. of product, making the total yield 10.0 g. (77%). Recrystallization from isopropanol produced a light yellow powder melting at 125°-127°. under reflux for 4.5 hours the solid was removed by filtration washed with ether providing 5.0 g refrigerated, providing another 5.0 g Recrystallization from isopropanol

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methanesulfonyl chloride (5.06 mL, 65.32 mmol) was added to a stirred solution of 3-[(4-amino)phenoxy]-1-propene (8.11 g, 54.43 mmol) in pyridine (80 mL) at 0° C. The mixture was stirred for 72 hours and was then poured slowly into ice-water and extracted with ether. The organic phase was washed with cold 1N HCl and was then extracted with 1N NaOH solution. The aqueous phase was acidified and the product (9.05 g, 73%) precipitated out as a white solid. extracted with ether The organic phase was washed with cold 1N HCl was then extracted with 1N NaOH solution the product (9.05 g, 73%) precipitated out as a white solid

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methanesulfonyl chloride (5.06 mL, 65.32 mmol) was added to a stirred solution of 3-[(4-amino)phenoxy]-1-propene (8.11 g, 54.43 mmol) in pyridine (80 mL) at 0° C. The mixture was stirred for 72 hours and was then poured slowly into ice-water and extracted with ether. The organic phase was washed with cold 1N HCl and was then extracted with 1N NaOH solution. The aqueous phase was acidified and the product (9.05 g, 73%) precipitated out as a white solid. extracted with ether The organic phase was washed with cold 1N HCl was then extracted with 1N NaOH solution the product (9.05 g, 73%) precipitated out as a white solid

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 3-[(4-nitro)phenoxy]-1-propene, prepared by the process of Example 1, Step 1, (12.65 g, 70.67 mmol) in concentrated HCl (85 mL) at 0° C., was slowly added stannous chloride (48 g, 212 mmol). After stirring for 20 minutes at 55° C., the mixture was cooled to 0° C. and carefully basified with 50% NaOH. The cloudy mixture was extracted with ether. The organic phase was decolorized (charcoal), dried (MgSO4), and concentrated to afford product (8.50 g, 81%) as a yellow oil which was used directly in the next step. the mixture was cooled to 0° C. The cloudy mixture was extracted with ether dried (MgSO4) concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methanesulfonyl chloride (5.06 mL, 65.32 mmol) was added to a stirred solution of 3-[(4-amino)phenoxy]-1-propene (8.11 g, 54.43 mmol) in pyridine (80 mL) at 0° C. The mixture was stirred for 72 hours and was then poured slowly into ice-water and extracted with ether. The organic phase was washed with cold 1N HCl and was then extracted with 1N NaOH solution. The aqueous phase was acidified and the product (9.05 g, 73%) precipitated out as a white solid. extracted with ether The organic phase was washed with cold 1N HCl was then extracted with 1N NaOH solution the product (9.05 g, 73%) precipitated out as a white solid

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 3-[(4-nitro)phenoxy]-1-propene prepared by the process of Example 1, Step 1, (12.65 g, 70.67 mmol) in concentrated HCl (85 mL) at 0° C. was slowly added stannous chloride (48 g, 212 mmol). After stirring for 20 minutes at 55° C., the mixture was cooled to 0° C. and carefully basified with 50% NaOH. The cloudy mixture was extracted with ether. The organic phase was decolorized (charcoal), dried (MgSO4), and concentrated to afford product (8.50 g, 81%) as a yellow oil which was used directly in the next step. the mixture was cooled to 0° C. The cloudy mixture was extracted with ether dried (MgSO4) concentrated

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 3-[(4-nitro)phenoxy]-1-propene prepared by the process of Example 1, Step 1, (12.65 g, 70.67 mmol) in concentrated HCl (85 mL) at 0° C. was slowly added stannous chloride (48 g, 212 mmol). After stirring for 20 minutes at 55° C., the mixture was cooled to 0° C. and carefully basified with 50% NaOH. The cloudy mixture was extracted with ether. The organic phase was decolorized (charcoal), dried (MgSO4), and concentrated to afford product (8.50 g, 81%) as a yellow oil which was used directly in the next step. the mixture was cooled to 0° C. The cloudy mixture was extracted with ether dried (MgSO4) concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-acetoxy-2-bromoquinolizinium bromide (10.0 g., 0.029 mole) in isopropanol (200 ml.) was added p-allyloxyaniline (11.0 g., 0.068 mole). The stirred mixture was boiled under reflux for 4.5 hours. The reaction mixture was cooled at room temperature overnight, and the solid was removed by filtration and washed with ether, providing 5.0 g. of product. The supernatant solution was treated with ether and refrigerated, providing another 5.0 g. of product, making the total yield 10.0 g. (77%). Recrystallization from isopropanol produced a light yellow powder melting at 125°-127°. under reflux for 4.5 hours the solid was removed by filtration washed with ether providing 5.0 g refrigerated, providing another 5.0 g Recrystallization from isopropanol

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-acetoxy-2-bromoquinolizinium bromide (10.0 g., 0.029 mole) in isopropanol (200 ml.) was added p-allyloxyaniline (11.0 g., 0.068 mole). The stirred mixture was boiled under reflux for 4.5 hours. The reaction mixture was cooled at room temperature overnight, and the solid was removed by filtration and washed with ether, providing 5.0 g. of product. The supernatant solution was treated with ether and refrigerated, providing another 5.0 g. of product, making the total yield 10.0 g. (77%). Recrystallization from isopropanol produced a light yellow powder melting at 125°-127°. under reflux for 4.5 hours the solid was removed by filtration washed with ether providing 5.0 g refrigerated, providing another 5.0 g Recrystallization from isopropanol