Реакция #9653

Уравнение реакции

methyl 4-(3′-methoxy-4′-nitro-1,1′-biphenyl-4-yl)-2,2-dimethyl -4-oxobutanoate

HCl

→

methyl 4-(4′-amino-3′-methoxy-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

Выход 67.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   Температураthe resulting suspension was heated
2. 2
   Температураat reflux for 2.5 h
3. 3
   Фильтрацияfiltered through a pad of Celite®
4. 4
   workup.ADDITIONWater was added
5. 5
   Экстракцияthe mixture was extracted with ethyl acetate
6. 6
   Сушкаthe combined organic phases were dried over anhydrous sodium sulfate
7. 7
   ДругоеSolvent was removed under reduced pressure
8. 8
   Другоеthe residue was triturated with ethyl acetate/hexane

Методика

To a solution of methyl 4-(3′-methoxy-4′-nitro-1,1′-biphenyl-4-yl)-2,2-dimethyl -4-oxobutanoate (670 mg, 1.80 mmol) in 85% aqueous ethanol (27 mL) was added iron powder (1.01 g, 18.04 mmol) and 2 N aqueous HCl (0.9 mL, 1.8 mmol), and the resulting suspension was heated at reflux for 2.5 h. The mixture was then cooled to rt, and filtered through a pad of Celite®. Water was added, the mixture was extracted with ethyl acetate, and the combined organic phases were dried over anhydrous sodium sulfate. Solvent was removed under reduced pressure and the residue was triturated with ethyl acetate/hexane to afford methyl 4-(4′-amino-3′-methoxy-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (410 mg, 67%). LC-MS ret. time 2.58 min, m/z 342.1 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.31 (s, 6H), 3.28 (s, 2H), 3.66 (s, 3H), 3.90 (s, 3H), 6.75 (d, 1H), 7.02–7.09 (m, 2H), 7.59 (d, 2H), 7.94 (d, 2H).

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