methyl 2-(3-bromoanilino)acetate

反応条件: temp:0.00; pressure:0.00; stir:

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 sodium nitrite (30 g) in water (200 ml) was added dropwise to a solution of N-(3-bromophenyl)glycine methyl ester (94 g) in aqueous acetic acid (850 ml) at 0°. After 1 h, methanol (200 ml) was added and the mixture was cooled to -10°. Zinc dust (351 g) was added portionwise over 2 h during which time the temperature was maintained at -10° to 0°. The mixture was then allowed to warm to room temperature, poured into ethyl acetate (1000 ml) and filtered. The filtrate was poured into water (1000 ml) and the layers were separated. The organic extract was washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate was added until the solution was basic. The aqueous extract was re-extracted using ethyl acetate (1000 ml) and the combined organic extracts were dried and evaporated. The residue was purified by FCC eluting with System A (1:1) to give the title compound (25.1 g) as an oil, t.l.c. (System A, 1:1) Rf 0.26. the mixture was cooled to -10° was maintained at -10° to 0° filtered The filtrate was poured into water (1000 ml) the layers were separated The organic extract was washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate was added until the solution The aqueous extract was re-extracted the combined organic extracts were dried evaporated The residue was purified by FCC eluting with System A (1:1)

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

実験手順: A mixture of 3-bromoaniline (88.6 g), methyl chloroacetate (44 ml), sodium acetate trihydrate (114 g) and methanol (70 ml) was heated under reflux for 18 h. The mixture was poured into water (500 ml) and extracted with dichloromethane (3×250 ml). The combined, dried organic extracts were evaporated and the residue was treated with 10% concentrated sulphuric acid in methanol (250 ml). After 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml). The resulting solid was filtered off, dissolved in dichloromethane (1000 ml), and this solution was dried and evaporated to give a solid (94 g). A portion of this solid (1 g) was purified by FCC eluting with System A (1:1) to give a semi-solid which was recrystallised from System A to give the title compound, m.p. 66°-68°. was heated under reflux for 18 h extracted with dichloromethane (3×250 ml) dried organic extracts were evaporated the residue was treated with 10% concentrated sulphuric acid in methanol (250 ml) After 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml) The resulting solid was filtered off dissolved in dichloromethane (1000 ml) this solution was dried evaporated

反応条件: temp:0.00; pressure:0.00; stir:

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 sodium nitrite (30 g) in water (200 ml) was added dropwise to a solution of N-(3-bromophenyl)glycine methyl ester (94 g) in aqueous acetic acid (850 ml) at 0°. After 1 h, methanol (200 ml) was added and the mixture was cooled to -10°. Zinc dust (351 g) was added portionwise over 2 h during which time the temperature was maintained at -10° to 0°. The mixture was then allowed to warm to room temperature, poured into ethyl acetate (1000 ml) and filtered. The filtrate was poured into water (1000 ml) and the layers were separated. The organic extract was washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate was added until the solution was basic. The aqueous extract was re-extracted using ethyl acetate (1000 ml) and the combined organic extracts were dried and evaporated. The residue was purified by FCC eluting with System A (1:1) to give the title compound (25.1 g) as an oil, t.l.c. (System A, 1:1) Rf 0.26. the mixture was cooled to -10° was maintained at -10° to 0° filtered The filtrate was poured into water (1000 ml) the layers were separated The organic extract was washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate was added until the solution The aqueous extract was re-extracted the combined organic extracts were dried evaporated The residue was purified by FCC eluting with System A (1:1)

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

実験手順: A mixture of 3-bromoaniline (88.6 g), methyl chloroacetate (44 ml), sodium acetate trihydrate (114 g) and methanol (70 ml) was heated under reflux for 18 h. The mixture was poured into water (500 ml) and extracted with dichloromethane (3×250 ml). The combined, dried organic extracts were evaporated and the residue was treated with 10% concentrated sulphuric acid in methanol (250 ml). After 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml). The resulting solid was filtered off, dissolved in dichloromethane (1000 ml), and this solution was dried and evaporated to give a solid (94 g). A portion of this solid (1 g) was purified by FCC eluting with System A (1:1) to give a semi-solid which was recrystallised from System A to give the title compound, m.p. 66°-68°. was heated under reflux for 18 h extracted with dichloromethane (3×250 ml) dried organic extracts were evaporated the residue was treated with 10% concentrated sulphuric acid in methanol (250 ml) After 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml) The resulting solid was filtered off dissolved in dichloromethane (1000 ml) this solution was dried evaporated

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

実験手順: A solution of sodium nitrite (30 g) in water (200 ml) was added dropwise to a solution of N-(3-bromophenyl)glycine methyl ester (94 g) in aqueous acetic acid (850 ml) at 0°. After 1 h, methanol (200 ml) was added and the mixture was cooled to -10°. Zinc dust (351 g) was added portionwise over 2 h during which time the temperature was maintained at -10° to 0°. The mixture was then allowed to warm to room temperature, poured into ethyl acetate (1000 ml) and filtered. The filtrate was poured into water (1000 ml) and the layers were separated. The organic extract was washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate was added until the solution was basic. The aqueous extract was re-extracted using ethyl acetate (1000 ml) and the combined organic extracts were dried and evaporated. The residue was purified by FCC eluting with System A (1:1) to give the title compound (25.1 g) as an oil, t.l.c. (System A, 1:1) Rf 0.26. the mixture was cooled to -10° was maintained at -10° to 0° filtered The filtrate was poured into water (1000 ml) the layers were separated The organic extract was washed with 2N sodium carbonate solution (500 ml) and solid sodium carbonate was added until the solution The aqueous extract was re-extracted the combined organic extracts were dried evaporated The residue was purified by FCC eluting with System A (1:1)

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

実験手順: A mixture of 3-bromoaniline (88.6 g), methyl chloroacetate (44 ml), sodium acetate trihydrate (114 g) and methanol (70 ml) was heated under reflux for 18 h. The mixture was poured into water (500 ml) and extracted with dichloromethane (3×250 ml). The combined, dried organic extracts were evaporated and the residue was treated with 10% concentrated sulphuric acid in methanol (250 ml). After 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml). The resulting solid was filtered off, dissolved in dichloromethane (1000 ml), and this solution was dried and evaporated to give a solid (94 g). A portion of this solid (1 g) was purified by FCC eluting with System A (1:1) to give a semi-solid which was recrystallised from System A to give the title compound, m.p. 66°-68°. was heated under reflux for 18 h extracted with dichloromethane (3×250 ml) dried organic extracts were evaporated the residue was treated with 10% concentrated sulphuric acid in methanol (250 ml) After 3 h the solution was poured carefully into 8% sodium bicarbonate (1200 ml) The resulting solid was filtered off dissolved in dichloromethane (1000 ml) this solution was dried evaporated