تفاعل #992761

معادلة التفاعل

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

sodium hydroxide

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title compound

المردود 76.0%

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

المردود 76.0%

المذيبات

ethanol

ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر