4-amino-5-chloro-2-fluorophenol

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

Procedure: To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%). The resulted mixture was stirred at 0° C. for 2 hours filtered

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

Procedure: To a solution of potassium 5-chloro-2-fluoro-4-nitrophenolate (1.0 g, 4.35 mmol, Yuxiang) in 95% EtOH (22 mL) and H2O (8 mL) was added Fe (0.97 g, 17.4 mmol) and NH4Cl (1.86 g, 34.8 mmol). The mixture was stirred at rt for 10 hours, then diluted with methanol (100 mL) and ethyl acetate (100 mL). Filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (50 mL) and ethyl acetate (50 mL). The organic phase was separated and the water phase was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a pale solid (0.6 g, 85.3%). Filtered the filtrate was concentrated in vacuo The residue was dissolved in water (50 mL) The organic phase was separated the water phase was extracted with ethyl acetate (50 mL×2) The combined organic layers were washed with brine (50 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%). The resulted mixture was stirred at 0° C. for 2 hours filtered

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

Procedure: To a solution of potassium 5-chloro-2-fluoro-4-nitrophenolate (1.0 g, 4.35 mmol) in 95% EtOH (22 mL) and H2O (8 mL) was added Fe (0.97 g, 17.4 mmol) and NH4Cl (1.86 g, 34.8 mmol). The mixture was stirred at rt for 10 hours, then diluted with methanol (100 mL) and ethyl acetate (100 mL). Filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (50 mL) and ethyl acetate (50 mL). The organic phase was separated and the water phase was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a pale solid (0.6 g, 85.3%). Filtered the filtrate was concentrated in vacuo The residue was dissolved in water (50 mL) The organic phase was separated the water phase was extracted with ethyl acetate (50 mL×2) The combined organic layers were washed with brine (50 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%). The resulted mixture was stirred at 0° C. for 2 hours filtered

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

Procedure: To a solution of potassium 5-chloro-2-fluoro-4-nitrophenolate (1.0 g, 4.35 mmol, Yuxiang) in 95% EtOH (22 mL) and H2O (8 mL) was added Fe (0.97 g, 17.4 mmol) and NH4Cl (1.86 g, 34.8 mmol). The mixture was stirred at rt for 10 hours, then diluted with methanol (100 mL) and ethyl acetate (100 mL). Filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (50 mL) and ethyl acetate (50 mL). The organic phase was separated and the water phase was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a pale solid (0.6 g, 85.3%). Filtered the filtrate was concentrated in vacuo The residue was dissolved in water (50 mL) The organic phase was separated the water phase was extracted with ethyl acetate (50 mL×2) The combined organic layers were washed with brine (50 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: To a solution of potassium 5-chloro-2-fluoro-4-nitrophenolate (1.0 g, 4.35 mmol, Yuxiang) in 95% EtOH (22 mL) and H2O (8 mL) was added Fe (0.97 g, 17.4 mmol) and NH4Cl (1.86 g, 34.8 mmol). The mixture was stirred at rt for 10 hours, then diluted with methanol (100 mL) and ethyl acetate (100 mL). Filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (50 mL) and ethyl acetate (50 mL). The organic phase was separated and the water phase was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a pale solid (0.6 g, 85.3%). Filtered the filtrate was concentrated in vacuo The residue was dissolved in water (50 mL) The organic phase was separated the water phase was extracted with ethyl acetate (50 mL×2) The combined organic layers were washed with brine (50 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%). The resulted mixture was stirred at 0° C. for 2 hours filtered

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

Procedure: To a solution of potassium 5-chloro-2-fluoro-4-nitrophenolate (1.0 g, 4.35 mmol, Yuxiang) in 95% EtOH (22 mL) and H2O (8 mL) was added Fe (0.97 g, 17.4 mmol) and NH4Cl (1.86 g, 34.8 mmol). The mixture was stirred at rt for 10 hours, then diluted with methanol (100 mL) and ethyl acetate (100 mL). Filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (50 mL) and ethyl acetate (50 mL). The organic phase was separated and the water phase was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a pale solid (0.6 g, 85.3%). Filtered the filtrate was concentrated in vacuo The residue was dissolved in water (50 mL) The organic phase was separated the water phase was extracted with ethyl acetate (50 mL×2) The combined organic layers were washed with brine (50 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%). The resulted mixture was stirred at 0° C. for 2 hours filtered

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

Procedure: To a solution of potassium 5-chloro-2-fluoro-4-nitrophenolate (1.0 g, 4.35 mmol) in 95% EtOH (22 mL) and H2O (8 mL) was added Fe (0.97 g, 17.4 mmol) and NH4Cl (1.86 g, 34.8 mmol). The mixture was stirred at rt for 10 hours, then diluted with methanol (100 mL) and ethyl acetate (100 mL). Filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (50 mL) and ethyl acetate (50 mL). The organic phase was separated and the water phase was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a pale solid (0.6 g, 85.3%). Filtered the filtrate was concentrated in vacuo The residue was dissolved in water (50 mL) The organic phase was separated the water phase was extracted with ethyl acetate (50 mL×2) The combined organic layers were washed with brine (50 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo

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

Procedure: To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%). The resulted mixture was stirred at 0° C. for 2 hours filtered