4-methylsulfonyl-3-(trifluoromethyl)aniline

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

Procedure: To a stirred suspension of 4-(methylsulfonyl)-3-(trifluoromethyl)aniline (1.04 g, 4.35 mmol) in conc. HCl (10 mL) was added dropwise a solution of sodium nitrate (0.315 g, 4.57 mmol) in water (10 mL) at −20° C. After stirring for 30 minutes, the resulting suspension was added Tin(II) chloride dihydrate (4.92 g, 21.8 mmol) in conc.HCl (10 mL) at −10° C. After stirring for 1 hour at −5° C., the mixture was stirred further 1 hour at room temperature. The reaction mixture was made alkaline with aqueous NaOH at 0-5° C. The mixture was filtered through Celite, the filterate was extracted with THF (30 mL×3), the combined organic layer washed with brine, dried over MgSO4 and concentration in vacuo to give the subtitle compound (1 g). at −10° C After stirring for 1 hour at −5° C. the mixture was stirred further 1 hour at room temperature at 0-5° C The mixture was filtered through Celite the filterate was extracted with THF (30 mL×3) the combined organic layer washed with brine dried over MgSO4 and concentration in vacuo

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

Procedure: A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.031 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield). was heated at reflux temperature for 1 hour After cooling insolubles were filtered off by Celite, and volatiles were removed by evaporation The residue was redissolved in ethyl acetate (50 mL) the whole washed with water and brine After dried over MgSO4 and concentration in vacuo The residue was washed with hexane

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

Procedure: A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.03.1 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield). was heated at reflux temperature for 1 hour After cooling insolubles were filtered off by Celite, and volatiles were removed by evaporation The residue was redissolved in ethyl acetate (50 mL) the whole washed with water and brine After dried over MgSO4 and concentration in vacuo The residue was washed with hexane

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

Procedure: To a stirred suspension of 4-(methylsulfonyl)-3-(trifluoromethyl)aniline (1.04 g, 4.35 mmol) in conc. HCl (10 mL) was added dropwise a solution of sodium nitrate (0.315 g, 4.57 mmol) in water (10 mL) at −20° C. After stirring for 30 minutes, the resulting suspension was added Tin(II) chloride dihydrate (4.92 g, 21.8 mmol) in conc.HCl (10 mL) at −10° C. After stirring for 1 hour at −5° C., the mixture was stirred further 1 hour at room temperature. The reaction mixture was made alkaline with aqueous NaOH at 0-5° C. The mixture was filtered through Celite, the filterate was extracted with THF (30 mL×3), the combined organic layer washed with brine, dried over MgSO4 and concentration in vacuo to give the subtitle compound (1 g). at −10° C After stirring for 1 hour at −5° C. the mixture was stirred further 1 hour at room temperature at 0-5° C The mixture was filtered through Celite the filterate was extracted with THF (30 mL×3) the combined organic layer washed with brine dried over MgSO4 and concentration in vacuo

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

Procedure: A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.031 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield). was heated at reflux temperature for 1 hour After cooling insolubles were filtered off by Celite, and volatiles were removed by evaporation The residue was redissolved in ethyl acetate (50 mL) the whole washed with water and brine After dried over MgSO4 and concentration in vacuo The residue was washed with hexane

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

Procedure: A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.031 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield). was heated at reflux temperature for 1 hour After cooling insolubles were filtered off by Celite, and volatiles were removed by evaporation The residue was redissolved in ethyl acetate (50 mL) the whole washed with water and brine After dried over MgSO4 and concentration in vacuo The residue was washed with hexane

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

Procedure: To a stirred suspension of 4-(methylsulfonyl)-3-(trifluoromethyl)aniline (1.04 g, 4.35 mmol) in conc. HCl (10 mL) was added dropwise a solution of sodium nitrate (0.315 g, 4.57 mmol) in water (10 mL) at −20° C. After stirring for 30 minutes, the resulting suspension was added Tin(II) chloride dihydrate (4.92 g, 21.8 mmol) in conc.HCl (10 mL) at −10° C. After stirring for 1 hour at −5° C., the mixture was stirred further 1 hour at room temperature. The reaction mixture was made alkaline with aqueous NaOH at 0-5° C. The mixture was filtered through Celite, the filterate was extracted with THF (30 mL×3), the combined organic layer washed with brine, dried over MgSO4 and concentration in vacuo to give the subtitle compound (1 g). at −10° C After stirring for 1 hour at −5° C. the mixture was stirred further 1 hour at room temperature at 0-5° C The mixture was filtered through Celite the filterate was extracted with THF (30 mL×3) the combined organic layer washed with brine dried over MgSO4 and concentration in vacuo

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

Procedure: A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.031 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield). was heated at reflux temperature for 1 hour After cooling insolubles were filtered off by Celite, and volatiles were removed by evaporation The residue was redissolved in ethyl acetate (50 mL) the whole washed with water and brine After dried over MgSO4 and concentration in vacuo The residue was washed with hexane

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

Procedure: To a stirred suspension of 4-(methylsulfonyl)-3-(trifluoromethyl)aniline (1.04 g, 4.35 mmol) in conc. HCl (10 mL) was added dropwise a solution of sodium nitrate (0.315 g, 4.57 mmol) in water (10 mL) at −20° C. After stirring for 30 minutes, the resulting suspension was added Tin(II) chloride dihydrate (4.92 g, 21.8 mmol) in conc.HCl (10 mL) at −10° C. After stirring for 1 hour at −5° C., the mixture was stirred further 1 hour at room temperature. The reaction mixture was made alkaline with aqueous NaOH at 0-5° C. The mixture was filtered through Celite, the filterate was extracted with THF (30 mL×3), the combined organic layer washed with brine, dried over MgSO4 and concentration in vacuo to give the subtitle compound (1 g). at −10° C After stirring for 1 hour at −5° C. the mixture was stirred further 1 hour at room temperature at 0-5° C The mixture was filtered through Celite the filterate was extracted with THF (30 mL×3) the combined organic layer washed with brine dried over MgSO4 and concentration in vacuo

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

Procedure: A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.031 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield). was heated at reflux temperature for 1 hour After cooling insolubles were filtered off by Celite, and volatiles were removed by evaporation The residue was redissolved in ethyl acetate (50 mL) the whole washed with water and brine After dried over MgSO4 and concentration in vacuo The residue was washed with hexane

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

Procedure: A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.03.1 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield). was heated at reflux temperature for 1 hour After cooling insolubles were filtered off by Celite, and volatiles were removed by evaporation The residue was redissolved in ethyl acetate (50 mL) the whole washed with water and brine After dried over MgSO4 and concentration in vacuo The residue was washed with hexane

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

Procedure: To a stirred suspension of 4-(methylsulfonyl)-3-(trifluoromethyl)aniline (1.04 g, 4.35 mmol) in conc. HCl (10 mL) was added dropwise a solution of sodium nitrate (0.315 g, 4.57 mmol) in water (10 mL) at −20° C. After stirring for 30 minutes, the resulting suspension was added Tin(II) chloride dihydrate (4.92 g, 21.8 mmol) in conc.HCl (10 mL) at −10° C. After stirring for 1 hour at −5° C., the mixture was stirred further 1 hour at room temperature. The reaction mixture was made alkaline with aqueous NaOH at 0-5° C. The mixture was filtered through Celite, the filterate was extracted with THF (30 mL×3), the combined organic layer washed with brine, dried over MgSO4 and concentration in vacuo to give the subtitle compound (1 g). at −10° C After stirring for 1 hour at −5° C. the mixture was stirred further 1 hour at room temperature at 0-5° C The mixture was filtered through Celite the filterate was extracted with THF (30 mL×3) the combined organic layer washed with brine dried over MgSO4 and concentration in vacuo