Реакция #9633

Уравнение реакции

methyl 4-[2-(4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate

HCl

→

methyl 4-[2-(4′-amino-1,1′-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate

Выход 91.4%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   Температураthe resulting mixture was refluxed for 2.5 h
2. 2
   ФильтрацияThe mixture was then filtered through a pad of Celite®
3. 3
   Экстракцияthe filtrate was extracted with dichloromethane
4. 4
   СушкаThe combined organic phases were then dried over anhydrous sodium sulfate
5. 5
   Концентрированиеconcentrated in vacuo

Методика

To a solution of methyl 4-[2-(4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate (1.24 g, 3.25 mmol) in 85% ethanol (50 mL) was added iron powder (1.81 g), followed by 2 N aqueous HCl (1.62 mL), and the resulting mixture was refluxed for 2.5 h. The mixture was then filtered through a pad of Celite® and the filtrate was extracted with dichloromethane. The combined organic phases were then dried over anhydrous sodium sulfate and concentrated in vacuo to afford methyl 4-[2-(4′-amino-1,1′-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate (1.05 g, 91%). LC-MS ret. time 2.20; m/z 354.0 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.57–1.66 (m, 2H), 2.09 (m, 2H), 3.28 (s, 2H), 3.61 (s, 3H), 3.64–3.71 (m, 4H), 6.76 (d, 2H), 7.42 (d, 2H), 7.54 (d, 2H), 7.88 (d, 2H).

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