4-amino-N-propan-2-ylbenzenesulfonamide

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

Procedure: To a stirred solution of 4-amino-N-isopropyl-benzenesulfonamide (4.0 g, 18.7 mmol) and 3-bromo-benzaldehyde (3.8 g, 20.5 mmol) in acetonitrile (150 mL) were added isobutene (6.5 mL, 93.5 mmoll) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (2.4 g, 3.7 mmol). The resulting mixture was stirred at 80° C. for 18 h in sealed tube. The mixture solution was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-40% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-sulfonic acid isopropylamide (3.8 g, 47.4%) as a light yellow solid: MS (ESI) M+1=437.1. washed with water (100 mL×2) and brine (100 mL×2) dried over anhydrous sodium sulfate The solvent was removed in vacuo the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-40% ethyl acetate in petroleum ether)

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

Procedure: To a stirred solution of N-isopropyl-4-nitro-benzenesulfonamide (9.0 g, 37.0 mmol) ethanol (500 mL) was added iron powder (11.0 g, 196.0 mmol) and the solution of ammonium chloride (22.0 g, 392.0 mmol) in water (150 mL). After the reaction mixture was refluxed for 3 h, the iron was filtered off and the filtrate was basified to pH 9 by addition of sodium carbonate. The reaction mixture was extracted with ethyl acetate (300 mL×2). The extract was washed with water (130 mL×2) and brine (130 mL×2), dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 20-60% ethyl acetate in petroleum ether) to afford 4-amino-N-isopropyl-benzenesulfonamide (7.0 g, 89%) as a yellow powder: MS (ESI) M+1=215. After the reaction mixture was refluxed for 3 h the iron was filtered off the filtrate was basified to pH 9 by addition of sodium carbonate The reaction mixture was extracted with ethyl acetate (300 mL×2) The extract was washed with water (130 mL×2) and brine (130 mL×2) dried over anhydrous sodium sulfate The solvent was removed in vacuo the residue was purified by ISCO combi-flash chromatography (gradient elution, 20-60% ethyl acetate in petroleum ether)