Reaktion #1870541

Reaktionsgleichung

N-(2,6-diisopropyl-4-nitro-phenyl)-4-methyl-benzenesulfonamide

sodium hydroxide

→

title compound

Ausbeute 76.0%

N-(4-Amino-2,6-diisopropyl-phenyl)-4-methyl-benzenesulfonamide

Ausbeute 76.0%

Lösungsmittel

ethanol

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONIt was then poured onto ice (300 mL)
2. 2
   FiltrationThe suspension was filtered
3. 3
   Extraktionextracted with ethyl acetate (3×100 mL)
4. 4
   TrocknenThe combined organic phases were dried over sodium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude product was purified by flash chromatography

Vorschrift

To a suspension of N-(2,6-diisopropyl-4-nitro-phenyl)-4-methyl-benzenesulfonamide (3.72 g) in ethanol (50 mL) was added stannous(II) chloride dihydrate (11.2 g) and the mixture was heated to 80° C. for 1.5 hour. It was then poured onto ice (300 mL), made strongly basic with solid sodium hydroxide (20 g) and diluted with ethyl acetate (100 mL). The suspension was filtered and extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 2.60 g (76%) of the title compound as an off-white solid. 1H NMR (500 MHz, CDCl3): 0.95 (d, 12H), 2.40 (s, 3H), 3.02 (m, 2H), 3.68 (b, 2H), 5.74 (s, 1H), 6.39 (s, 2H), 7.23 (d, 2H), 7.60 (d, 2H).

Quelle