methyl 3-amino-5-bromo-2-chlorobenzoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of methyl 3-amino-5-bromo-2-chlorobenzoate (2.8 g, 10.6 mmol) and cyclopentanone (4.47 g, 53.2 mmol) in methanol (20 mL) was added acetic acid (1.3 mL, 21.2 mmol) and the reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.7 g, 26.6 mmol) was added and the reaction stirred overnight. On completion, the solvent was removed under reduced pressure and the product was purified by column chromatography to afford methyl 5-bromo-2-chloro-3-(cyclopentylamino)benzoate (0.5 g, 14.2%). the reaction stirred overnight On completion, the solvent was removed under reduced pressure the product was purified by column chromatography

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To stirred solution of methyl 5-bromo-2-chloro-3-nitrobenzoate (3.4 g, 11.6 mmol) in ethanol (19 mL) was added ammonium chloride (3.4 g, 57.8 mmol) dissolved in water (30 mL) and iron powder (5.16 g, 92.5 mmol). The reaction mixture was heated at 80° C. for 1 h. On completion, the reaction mixture was filtered through celite washing with ethanol and ethylacetate. The filtrate was extracted with ethyl acetate and the combined organic layers were washed with water, dried and concentrated under reduced pressure to give methyl 3-amino-5-bromo-2-chlorobenzoate (2.8 g, 92.1%). On completion, the reaction mixture was filtered through celite washing with ethanol and ethylacetate The filtrate was extracted with ethyl acetate the combined organic layers were washed with water dried concentrated under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To stirred solution of methyl 5-bromo-2-chloro-3-nitrobenzoate (3.4 g, 11.6 mmol) in ethanol (19 mL) was added ammonium chloride (3.4 g, 57.8 mmol) dissolved in water (30 mL) and iron powder (5.16 g, 92.5 mmol). The reaction mixture was heated at 80° C. for 1 h. On completion, the reaction mixture was filtered through celite washing with ethanol and ethylacetate. The filtrate was extracted with ethyl acetate and the combined organic layers were washed with water, dried and concentrated under reduced pressure to give methyl 3-amino-5-bromo-2-chlorobenzoate (2.8 g, 92.1%). On completion, the reaction mixture was filtered through celite washing with ethanol and ethylacetate The filtrate was extracted with ethyl acetate the combined organic layers were washed with water dried concentrated under reduced pressure