methyl 3-amino-4-hydroxy-5-iodobenzoate

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: To an ice-cold, stirred solution of Methyl 3-amino-4-hydroxy-5-iodobenzoate (2.3 g) and sodium bicarbonate (1.5 g) in 1:1 isobutyl methyl ketone/water (80 mL) was added chloroacetyl chloride (1.1 g), and the reaction mixture was stirred for 1 h. The mixture was warmed to room temperature and heated at reflux for 18 h. After overnight, a beige solid formed. The mixture was filtered, and washed with water and hexanes to give 2.4 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 10.98, 7.89, 7.47, 4.79, 3.82. heated at reflux for 18 h After overnight a beige solid formed The mixture was filtered washed with water and hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of methyl 4-hydroxy-3-iodo-5-nitrobenzoate (2.99 g) in ethanol (40 mL) was added tin (II) chloride (10 g) portion wise. After stirring for 1 h at reflux, the mixture was cooled to 0° C. and quenched by saturated potassium carbonate (100 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 2.5 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.50, 7.24, 3.75. at reflux quenched by saturated potassium carbonate (100 mL) The mixture was filtered through diatomaceous earth the filtrate was extracted with ethyl acetate (4×100 mL) The combined organic extracts were dried (sodium sulfate) filtered concentrated under reduced pressure

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

実験手順: To an ice-cold, stirred solution of Methyl 3-amino-4-hydroxy-5-iodobenzoate (2.3 g) and sodium bicarbonate (1.5 g) in 1:1 isobutyl methyl ketone/water (80 mL) was added chloroacetyl chloride (1.1 g), and the reaction mixture was stirred for 1 h. The mixture was warmed to room temperature and heated at reflux for 18 h. After overnight, a beige solid formed. The mixture was filtered, and washed with water and hexanes to give 2.4 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 10.98, 7.89, 7.47, 4.79, 3.82. heated at reflux for 18 h After overnight a beige solid formed The mixture was filtered washed with water and hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of methyl 4-hydroxy-3-iodo-5-nitrobenzoate (2.99 g) in ethanol (40 mL) was added tin (II) chloride (10 g) portion wise. After stirring for 1 h at reflux, the mixture was cooled to 0° C. and quenched by saturated potassium carbonate (100 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 2.5 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.50, 7.24, 3.75. at reflux quenched by saturated potassium carbonate (100 mL) The mixture was filtered through diatomaceous earth the filtrate was extracted with ethyl acetate (4×100 mL) The combined organic extracts were dried (sodium sulfate) filtered concentrated under reduced pressure

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of methyl 4-hydroxy-3-iodo-5-nitrobenzoate (2.99 g) in ethanol (40 mL) was added tin (II) chloride (10 g) portion wise. After stirring for 1 h at reflux, the mixture was cooled to 0° C. and quenched by saturated potassium carbonate (100 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 2.5 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.50, 7.24, 3.75. at reflux quenched by saturated potassium carbonate (100 mL) The mixture was filtered through diatomaceous earth the filtrate was extracted with ethyl acetate (4×100 mL) The combined organic extracts were dried (sodium sulfate) filtered concentrated under reduced pressure

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

実験手順: To an ice-cold, stirred solution of Methyl 3-amino-4-hydroxy-5-iodobenzoate (2.3 g) and sodium bicarbonate (1.5 g) in 1:1 isobutyl methyl ketone/water (80 mL) was added chloroacetyl chloride (1.1 g), and the reaction mixture was stirred for 1 h. The mixture was warmed to room temperature and heated at reflux for 18 h. After overnight, a beige solid formed. The mixture was filtered, and washed with water and hexanes to give 2.4 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 10.98, 7.89, 7.47, 4.79, 3.82. heated at reflux for 18 h After overnight a beige solid formed The mixture was filtered washed with water and hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of methyl 4-hydroxy-3-iodo-5-nitrobenzoate (2.99 g) in ethanol (40 mL) was added tin (II) chloride (10 g) portion wise. After stirring for 1 h at reflux, the mixture was cooled to 0° C. and quenched by saturated potassium carbonate (100 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 2.5 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.50, 7.24, 3.75. at reflux quenched by saturated potassium carbonate (100 mL) The mixture was filtered through diatomaceous earth the filtrate was extracted with ethyl acetate (4×100 mL) The combined organic extracts were dried (sodium sulfate) filtered concentrated under reduced pressure

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: To an ice-cold, stirred solution of Methyl 3-amino-4-hydroxy-5-iodobenzoate (2.3 g) and sodium bicarbonate (1.5 g) in 1:1 isobutyl methyl ketone/water (80 mL) was added chloroacetyl chloride (1.1 g), and the reaction mixture was stirred for 1 h. The mixture was warmed to room temperature and heated at reflux for 18 h. After overnight, a beige solid formed. The mixture was filtered, and washed with water and hexanes to give 2.4 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 10.98, 7.89, 7.47, 4.79, 3.82. heated at reflux for 18 h After overnight a beige solid formed The mixture was filtered washed with water and hexanes

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of methyl 4-hydroxy-3-iodo-5-nitrobenzoate (2.99 g) in ethanol (40 mL) was added tin (II) chloride (10 g) portion wise. After stirring for 1 h at reflux, the mixture was cooled to 0° C. and quenched by saturated potassium carbonate (100 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 2.5 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.50, 7.24, 3.75. at reflux quenched by saturated potassium carbonate (100 mL) The mixture was filtered through diatomaceous earth the filtrate was extracted with ethyl acetate (4×100 mL) The combined organic extracts were dried (sodium sulfate) filtered concentrated under reduced pressure

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

実験手順: To an ice-cold, stirred solution of Methyl 3-amino-4-hydroxy-5-iodobenzoate (2.3 g) and sodium bicarbonate (1.5 g) in 1:1 isobutyl methyl ketone/water (80 mL) was added chloroacetyl chloride (1.1 g), and the reaction mixture was stirred for 1 h. The mixture was warmed to room temperature and heated at reflux for 18 h. After overnight, a beige solid formed. The mixture was filtered, and washed with water and hexanes to give 2.4 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 10.98, 7.89, 7.47, 4.79, 3.82. heated at reflux for 18 h After overnight a beige solid formed The mixture was filtered washed with water and hexanes