تفاعل #9653

معادلة التفاعل

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

المردود 67.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe resulting suspension was heated
2. 2
   درجة الحرارةat reflux for 2.5 h
3. 3
   ترشيحfiltered through a pad of Celite®
4. 4
   workup.ADDITIONWater was added
5. 5
   استخلاصthe mixture was extracted with ethyl acetate
6. 6
   تجفيفthe combined organic phases were dried over anhydrous sodium sulfate
7. 7
   أخرىSolvent was removed under reduced pressure
8. 8
   أخرىthe residue was triturated with ethyl acetate/hexane

الإجراء التجريبي

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).

المصدر